2025, 高分子科学功績賞　　　　　　　　　　　　　　　

2018, Molecular Chirality Award　　　　　　　　　　　　　　　
MONDE Kenji

1992, 第7回若い世代の特別講演賞　　　　　　　　　　　　　　　
Japan

1992, September, 1992 7th Special Lecture Award for the younger generation (The Chemical Society of Japan)　　　　　　　　　　　　　　　

Shortwave Infrared (SWIR)-Emitting Tamoxifen-Conjugated Cyanine Dyes for Estrogen Receptor-Targeted Cancer Imaging
Aravind Kanda Swamy, Mahadeva M. M. Swamy, Kohei Yuyama, Takeshi Jin, Kenji Monde
ACS Medicinal Chemistry Letters, 16, 8, 1641, 1647, American Chemical Society (ACS), Jul. 2025, [Peer-reviewed], [International Magazine]
English, Scientific journal

Enantioselective Synthesis of Axially Chiral 1,8-Diarylnaphthalenes by Rh-Catalyzed [2 + 2 + 2] Cycloaddition and Evaluation of Their Chiroptical Properties
Takanori Shibata, Hinako Nikawa, Ema Kadosaka, Mamoru Ito, Tohru Taniguchi, Kenji Monde
Organic Letters, 27, 17, 4524, 4528, American Chemical Society (ACS), Apr. 2025, [Peer-reviewed], [International Magazine]
English, Scientific journal

Asymmetric Synthesis of Noradamantane Scaffolds via Diphenylprolinol Silyl Ether‐Mediated Domino Michael/Epimerization/Michael (or Aldol)/1,2‐Addition Reactions
Konstantinos Daskalakis, Nariyoshi Umekubo, Satrajit Indu, Genki Kawauchi, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi
Angewandte Chemie International Edition, 64, 23, Wiley, Apr. 2025, [Peer-reviewed], [International Magazine]
English, Scientific journal, Abstract

Topologically unique chiral noradamantanes are synthesized using a diphenylprolinol silyl ether‐mediated domino Michael/epimerization/Michael/1,2‐addition or Michael/epimerization/aldol/1,2‐addition reaction with excellent enantioselectivity in a single reaction vessel. Three carbon–carbon bonds are formed, and six chiral centers, including one all‐carbon quaternary center, are generated, five of which are fully controlled. These functionalized noradamantanes are 3D, cage‐like molecules that can serve as valuable chiral building blocks for drug design.

Malabaricone C isolated from edible plants as a potential inhibitor of SARS-CoV-2 infection.
Mutmainah, Yuta Murai, Ai Fujimoto, Rintaro Kawamura, Akira Kitamura, Sajeer Koolath, Seigo Usuki, Michihito Sasaki, Yasuko Orba, Yasuyuki Igarashi, Hirofumi Sawa, Akihiko Sato, Kenji Monde
Scientific reports, 15, 1, 8518, Mar. 2025, [Peer-reviewed], [International Magazine]
English, Scientific journal, Although the SARS-CoV-2 epidemic worldwide has gradually decreased, in some areas, the situation has not yet been stamped and has become a global health emergency. It is quite possible that we could again be threatened by a new coronavirus. Therefore, new nucleotide analog drugs and vaccines or using drug repositioning for SARS-CoV-2 still has been developed, yet their safety and efficacy against COVID-19 remains underexplored. Malabaricone C is 2,6-dihydroxyphenyl acylphenol found in edible plants such as the mace spice of nutmeg derived from the seeds of Myristica fragrans. In this study, we identified malabaricone C as the first inhibitor of SARS-CoV-2 from natural food with a safe alternative for drugs. Malabaricone C and its chemical derivatives showed EC50 values of 1-1.5 μM against SARS-CoV-2 (WK-521, ancestral strain) and its variant strains in mammalian cells (HEK293T and Vero E6). In addition, we have successfully established novel evaluation system for the inhibition of SARS virus cell fusion by visualization for providing a versatile tool for study SARS-CoV-2 mediated fusion. Furthermore, our experiments suggested that malabaricone C could affect the distribution of sphingomyelin on the plasma membrane, which involves in viral infections. Thus, in light of the beneficial effect of malabaricone C on viral infection, the nontoxic malabaricone C is a suitable candidate as a drug that can be employed in the treatment and prevention of COVID-19. Moreover, it may potentially be used to treat acute infections of other enveloped viruses.

Enantioselective Synthesis of α‐Trifluoromethyl tert‐Alcohols and Amines via Organocatalyst‐Mediated Aldol and Mannich Reactions
Yujiro Hayashi, Hinata Odaira, Masashi Tomikawa, Naoki Mori, Tohru Taniguchi, Kenji Monde
Asian Journal of Organic Chemistry, 14, 4, e202500035, Wiley, Feb. 2025, [Peer-reviewed], [International Magazine]
English, Scientific journal, Abstract

The asymmetric aldol reaction of ethyl trifluoropyruvate with aldehydes was developed using diarylprolinol as a catalyst, affording α‐trifluoromethyl‐substituted tertiary alcohols with high enantioselectivity. Similarly, the asymmetric Mannich reaction of aldehydes with an imine derived from ethyl trifluoropyruvate was developed using diphenylprolinol silyl ether in combination with an acid, yielding α‐trifluoromethyl‐substituted tertiary amines. The absolute and relative configurations of the products were determined by vibrational circular dichroism (VCD).

Scalable preparation of furanosteroidal viridin, β-viridin and viridiol from Trichoderma virens
Wen Zhang, Kazu Sunami, Shuo Liu, Desita Triana, Zetryana Puteri Tachrim, Rikuto Kikuchi, Tohru Taniguchi, Kenji Monde, Tsunayoshi Takehara, Da-Yang Zhou, Takeyuki Suzuki, Yasuyuki Hashidoko, Makoto Hashimoto, Yuta Murai
Scientific Reports, 15, 1, 3110, Springer Science and Business Media LLC, Jan. 2025, [Peer-reviewed], ［Internationally co-authored］, [International Magazine]
English, Scientific journal

Screening of a Fraction with Higher Amyloid β Aggregation Inhibitory Activity from a Library Containing 210 Mushroom Extracts Using a Microliter-Scale High-Throughput Screening System with Quantum Dot Imaging
Gegentuya Huanood, Mahadeva M. M. Swamy, Rina Sasaki, Keiya Shimamori, Masahiro Kuragano, Enkhmaa Enkhbat, Yoshiko Suga, Masaki Anetai, Kenji Monde, Kiyotaka Tokuraku
Foods, 13, 23, 3740, 3740, MDPI AG, Nov. 2024, [Peer-reviewed], [International Magazine]
English, Scientific journal, Alzheimer’s disease (AD) is a highly prevalent neurodegenerative disease hallmarked by amyloid plaques and neurofibrillary tangles. Amyloid plaques are formed by the amyloid β (Aβ) aggregation, so substances that inhibit this aggregation are useful for preventing and treating AD. Mushrooms are widely used medicinal fungi with high edible and nutritional value. Mushrooms have a variety of biologically active ingredients, and studies have shown that they have certain effects in anti-bacterial, anti-oxidation, anti-inflammatory, anti-tumor, and immune regulation. Previously, we developed a microliter-scale high-throughput screening (MSHTS) system using quantum dot (QD) nanoprobes to screen Aβ aggregation inhibitors. In this study, we appraised the Aβ aggregation inhibitory activity of 210 natural mushrooms from Hokkaido (Japan) and found 11 samples with high activity. We then selected Elfvingia applanata and Fuscoporia obliqua for extraction and purification as these samples were able to suppress Aβ-induced neurocytotoxicity and were readily available in large quantities. We found that the ethyl acetate (EtOAc) extract of E. applanata has high Aβ aggregation inhibitory activity, so we performed silica gel column chromatography fractionation and found that fraction 5 (f5) of the EtOAc extract displayed the highest Aβ aggregation inhibitory activity among all mushroom samples. The half-maximal effective concentration (EC50) value was 2.30 µg/mL, higher than the EC50 of 10.7 µg/mL for rosmarinic acid, a well-known Aβ aggregation inhibitor. This inhibitory activity decreased with further purification, suggesting that some compounds act synergistically. The f5 fraction also inhibited the deposition of Aβ aggregates on the cell surface of human neuroblastoma SH-SY5Y cells. Our expectation is that f5, with additional tests, may eventually prove to be an inhibitor for the prevention of AD.

Testing the Simplified Molecular Dynamics Approach to Improve the Reproduction of ECD Spectra and Monitor Aggregation
Attila Mándi, Aliz Rimóczi, Andrea Vasas, Judit Hohmann, Mahadeva M. M. Swamy, Kenji Monde, Roland A. Barta, Máté Kicsák, István Komáromi, Krisztina Fehér, Tibor Kurtán
International Journal of Molecular Sciences, 25, 12, 6453, MDPI AG, Jun. 2024, [Peer-reviewed], ［Internationally co-authored］, [International Magazine]
English, Scientific journal, A simplified molecular-dynamics-based electronic circular dichroism (ECD) approach was tested on three condensed derivatives with limited conformational flexibility and an isochroman-2H-chromene hybrid, the ECD spectra of which could not be precisely reproduced by the conventional ECD calculation protocol. Application of explicit solvent molecules at the molecular mechanics (MD) level in the dynamics simulations and subsequent TDDFT-ECD calculation for the unoptimized MD structures was able to improve the agreements between experimental and computed spectra. Since enhancements were achieved even for molecules with limited conformational flexibility, deformations caused by the solvent molecules and multitudes of conformers produced with unoptimized geometries seem to be key factors for better agreement. The MD approach could confirm that aggregation of the phenanthrene natural product luzulin A had a significant contribution to a specific wavelength range of the experimental ECD. The MD approach has proved that dimer formation occurred in solution and this was responsible for the anomalous ECD spectrum. The scope and limitations of the method have also been discussed.

Determination of N‐centered stereochemistry in N22‐methylated chlorophyll‐a derivatives and their epimer‐dependent optical spectra
Riko Ataka, Tohru Taniguchi, Kenji Monde, Hitoshi Tamiaki
Chirality, 36, 6, e23681, Wiley, Jun. 2024, [Peer-reviewed], [International Magazine]
English, Scientific journal, Abstract

An N‐centered epimeric mixture of chlorophyll‐a derivatives methylated at the inner nitrogen atom was separated by reverse‐phase high‐performance liquid chromatography. Circular dichroism (CD) spectroscopic analyses of the epimerically pure N22‐methyl‐chlorins revealed that the minor first‐eluted and major second‐eluted stereoisomers were (22S)‐ and (22R)‐configurations, respectively. Their visible absorption and CD spectra in solution were dependent on the N22‐stereochemistry. The epimer‐dependent spectral changes were independent of the substituents at the peripheral 3‐position of the core chlorin chromophore.

Isolation and Structure Determination of cis-OPDA-α-Monoglyceride from Arabidopsis thaliana
Shotaro Hirota, Yusuke Ito, Shiro Inoue, Naoki Kitaoka, Tohru Taniguchi, Kenji Monde, Kosaku Takahashi, Hideyuki Matsuura
Journal of Natural Products, 87, 5, 1358, 1367, American Chemical Society (ACS), Apr. 2024, [Peer-reviewed], [International Magazine]
English, Scientific journal

Biocompatible and Water-Soluble Shortwave-Infrared (SWIR)-Emitting Cyanine-Based Fluorescent Probes for In Vivo Multiplexed Molecular Imaging
Mahadeva M. M. Swamy, Yuta Murai, Kenji Monde, Setsuko Tsuboi, Aravind K. Swamy, Takashi Jin
ACS Applied Materials & Interfaces, 16, 14, 17253, 17266, American Chemical Society (ACS), Apr. 2024, [Peer-reviewed], [International Magazine]
English, Scientific journal

Racemization of the substrate and product by serine palmitoyltransferase from Sphingobacterium multivorum yields two enantiomers of the product from d-serine
Hiroko Ikushiro, Takumi Honda, Yuta Murai, Taiki Murakami, Aya Takahashi, Taiki Sawai, Haruna Goto, Shin-ichi Ikushiro, Ikuko Miyahara, Yoshio Hirabayashi, Nobuo Kamiya, Kenji Monde, Takato Yano
Journal of Biological Chemistry, 300, 3, 105728, Elsevier BV, Mar. 2024, [Peer-reviewed], [International Magazine]
English, Scientific journal

Photoinduced dual bond rotation of a nitrogen-containing system realized by chalcogen substitution
Shotaro Nagami, Rintaro Kaguchi, Taichi Akahane, Yu Harabuchi, Tohru Taniguchi, Kenji Monde, Satoshi Maeda, Satoshi Ichikawa, Akira Katsuyama
Nature Chemistry, 16, 6, 959, 969, Springer Science and Business Media LLC, Feb. 2024, [Peer-reviewed], [International Magazine]
English, Scientific journal

Stereochemistry of Sphingolipids in Ganglioside GM3 Enhances Recovery of Nervous Functionality
Sajeer Koolath, Yuta Murai, Tomoya Suzuki, Mahadeva M. M. Swamy, Seigo Usuki, Kenji Monde
ACS Medicinal Chemistry Letters, 14, 9, 1237, 1241, American Chemical Society (ACS), Aug. 2023, [Peer-reviewed], [International Magazine]
English, Scientific journal

Structural insights into the substrate recognition of serine palmitoyltransferase from Sphingobacterium multivorum
Hiroko Ikushiro, Taiki Murakami, Aya Takahashi, Asuka Katayama, Taiki Sawai, Haruna Goto, Sajeer Koolath, Yuta Murai, Kenji Monde, Ikuko Miyahara, Nobuo Kamiya, Takato Yano
Journal of Biological Chemistry, 299, 5, 104684, 104684, Elsevier BV, May 2023, [Peer-reviewed]
Scientific journal

Stereochemistry‐activity relationship of ceramide‐induced exosome production to clear amyloid‐β in Alzheimer's disease
Mariam Abdelrasoul, Kohei Yuyama, Mahadeva M. M. Swamy, Yuta Murai, Kenji Monde
Chirality, 35, 9, 577, 585, Wiley, Apr. 2023, [Peer-reviewed]
English, Scientific journal, Abstract

Stereochemistry has a substantial impact on the biological activity of various drugs. We investigated the role of stereochemistry of ceramides in inducing the production of exosomes, a type of extracellular vesicle, from neuronal cells, with a potential benefit in improving the clearance of amyloid‐β (Aβ), a causal agent of Alzheimer's disease. A stereochemical library of diverse ceramides with different tail lengths was synthesized with the purpose of varying stereochemistry (D‐erythro: DE, D‐threo: DT, L‐erythro: LE, L‐threo: LT) and hydrophobic tail length (C6, C16, C18, C24). The exosome levels were quantified using TIM4‐based exosome enzyme‐linked immunosorbent assay after concentrating the conditioned medium using centrifugal filter devices. The results revealed a pivotal role of stereochemistry in determining the biological activity of ceramide stereoisomers, with the superiority of those based on DE and DT stereochemistry with C16 and C18 tails, which demonstrated significantly higher exosome production, without a significant change in the particle size of the released exosomes. In transwell experiments with Aβ‐expressed neuronal and microglial cells, DE‐ and DT‐ceramides with C16 and C18 tails significantly decreased extracellular Aβ levels. The results reported here are promising in the design of non‐classic therapies for the treatment of Alzheimer's disease.

Total Synthesis, Absolute Configuration, and Phytotoxic Activity of Foeniculoxin
Akane Yamagishi, Yuki Egoshi, Makoto T. Fujiwara, Noriyuki Suzuki, Tohru Taniguchi, Ryuuichi D. Itoh, Yumiko Suzuki, Yoshiro Masuyama, Kenji Monde, Toyonobu Usuki
Chemistry – A European Journal, 29, 8, e202203396, Wiley, Feb. 2023, [Peer-reviewed]
English, Scientific journal, Abstract

Foeniculoxin is a major phytotoxin produced by Italian strains of Phomopsis foeniculi. The first total synthesis is described utilizing the ene reaction and Sonogashira cross‐coupling reaction as key steps. The absolute configuration of the C6’ was determined using chiral separation and an advanced Mosher's method. The phytotoxicity of the synthesized compound was demonstrated via syringe‐based infiltration into Chenopodium album and Arabidopsis thaliana leaves. Synthetic foeniculoxin induced various defects in A. thaliana leaf cells before lesion formation, including protein leakage into the cytoplasm from both chloroplasts and mitochondria and mitochondrial rounding and swelling. Furthermore, foeniculoxin and the antibiotic hygromycin B caused similar agglomeration of mitochondria around chloroplasts, highlighting this event as a common component in the early stages of plant cell death.

Stereoselective Construction of Fluorinated Quaternary Stereogenic Centers via an Organocatalytic Asymmetric exo-Selective Diels–Alder Reaction in the Presence of Water
Bojan P. Bondzić, Konstantinos Daskalakis, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi
Organic Letters, 24, 40, 7455, 7460, American Chemical Society (ACS), Oct. 2022, [Peer-reviewed]
Scientific journal

Immuno-digital invasive cleavage assay for analyzing Alzheimer's amyloid ß-bound extracellular vesicles.
Kohei Yuyama, Hui Sun, Yasuyuki Igarashi, Kenji Monde, Takumi Hirase, Masato Nakayama, Yoichi Makino
Alzheimer's research & therapy, 14, 1, 140, 140, Oct. 2022, [Peer-reviewed], [International Magazine]
English, Scientific journal, BACKGROUND: The protracted preclinical stage of Alzheimer's disease (AD) provides the opportunity for early intervention to prevent the disease; however, the lack of minimally invasive and easily detectable biomarkers and their measurement technologies remain unresolved. Extracellular vesicles (EVs) are nanosized membrane vesicles released from a variety of cells and play important roles in cell-cell communication. Neuron-derived and ganglioside-enriched EVs capture amyloid-ß protein, a major AD agent, and transport it into glial cells for degradation; this suggests that EVs influence Aß accumulation in the brain. EV heterogeneity, however, requires the use of a highly sensitive technique for measuring specific EVs in biofluid. In this study, immuno-digital invasive cleavage assay (idICA) was developed for quantitating target-intact EVs. METHODS: EVs were captured onto ganglioside GM1-specific cholera toxin B subunit (CTB)-conjugated magnetic beads and detected with a DNA oligonucleotide-labeled Aß antibody. Fluorescence signals for individual EVs were then counted using an invasive cleavage assay (ICA). This idICA examines the Aß-bound and GM1-containing EVs isolated from the culture supernatant of human APP-overexpressing N2a (APP-N2a) cells and APP transgenic mice sera. RESULTS: The idICA quantitatively detected Aß-bound and GM1-containing EVs isolated from culture supernatants of APP-N2a cells and sera of AD model mice. The idICA levels of Aß-associated EVs in blood gradually increased from 3- to 12-month-old mice, corresponding to the progression of Aß accumulations in the brain of AD model mice. CONCLUSIONS: The present findings suggest that peripheral EVs harboring Aß and GM1 reflect Aß burden in mice. The idICA is a valuable tool for easy quantitative detection of EVs as an accessible biomarker for preclinical AD diagnosis.

Evaluation of Plant Ceramide Species-Induced Exosome Release from Neuronal Cells and Exosome Loading Using Deuterium Chemistry
Yuta Murai, Takumi Honda, Kohei Yuyama, Daisuke Mikami, Koichi Eguchi, Yuichi Ukawa, Seigo Usuki, Yasuyuki Igarashi, Kenji Monde
International Journal of Molecular Sciences, 23, 18, 10751, 10751, MDPI AG, Sep. 2022, [Peer-reviewed], [International Magazine]
English, Scientific journal, The extracellular accumulation of aggregated amyloid-β (Aβ) in the brain leads to the early pathology of Alzheimer’s disease (AD). The administration of exogenous plant-type ceramides into AD model mice can promote the release of neuronal exosomes, a subtype of extracellular vesicles, that can mediate Aβ clearance. In vitro studies showed that the length of fatty acids in mammalian-type ceramides is crucial for promoting neuronal exosome release. Therefore, investigating the structures of plant ceramides is important for evaluating the potential in releasing exosomes to remove Aβ. In this study, we assessed plant ceramide species with D-erythro-(4E,8Z)-sphingadienine and D-erythro-(8Z)-phytosphingenine as sphingoid bases that differ from mammalian-type species. Some plant ceramides were more effective than mammalian ceramides at stimulating exosome release. In addition, using deuterium chemistry-based lipidomics, most exogenous plant ceramides were confirmed to be derived from exosomes. These results suggest that the ceramide-dependent upregulation of exosome release may promote the release of exogenous ceramides from cells, and plant ceramides with long-chain fatty acids can effectively release neuronal exosomes and prevent AD pathology.

Penta-deuterium-labeled 4E, 8Z-sphingadienine for rapid analysis in sphingolipidomics study
Yuta Murai, Kohei Yuyama, Daisuke Mikami, Yasuyuki Igarashi, Kenji Monde
Chemistry and Physics of Lipids, 245, 105202, 105202, Elsevier BV, Jul. 2022, [Peer-reviewed], [International Magazine]
English, Scientific journal, The use of deuterium-incorporated bioactive compounds is an efficient method for tracing their metabolic fate and for quantitative analysis by mass spectrometry without complicated HPLC separation even if their amounts are extremely small. Plant sphingolipids and their metabolites, which have C4, 8-olefins on a common backbone as a sphingoid base, show unique and fascinating bioactivities compared to those of sphingolipids in mammals. However, the functional and metabolic mechanisms of exogenous plant sphingolipids have not been elucidated due to the difficulty in distinguishing exogenous sphingolipids from endogenous sphingolipids having the same polarity and same molecular weight by mass spectrometric analysis. Their roles might be elucidated by the use of deuterated probes with original biological and physicochemical properties. In this study, we designed (2S,3R,4E,8Z)-2-aminooctadeca-4,8-diene-17,17,18,18,18-d5-1,3-diol (penta-deuterium-labeled 4E, 8Z-sphingadienine) as a tracer for exogenous metabolic studies. In addition, the sphingadienine was confirmed to be metabolized in HEK293 cells and showed distinct peaks in mass spectrometric analysis.

Control of Reactions of Pyruvates by Catalysts: Direct Enantioselective Mannich Reactions of Pyruvates Catalyzed by Amine-based Catalyst Systems
Santanu Mondal, Ravindra D. Aher, Venkati Bethi, Yu-Ju Lin, Tohru Taniguchi, Kenji Monde, Fujie Tanaka
Organic Letters, 24, 9, 1853, 1858, American Chemical Society (ACS), Mar. 2022, [Peer-reviewed]
English, Scientific journal

Evaluation of chiral N , N ‐dimethyl‐sphingosine for the interaction between nerve growth factor and tropomyosin receptor kinase A
Yuta Murai, Akihiro Sekiguchi, Taeko Hirakawa, Seigo Usuki, Yasuyuki Igarashi, Kenji Monde
Chirality, 34, 807, 812, Wiley, Feb. 2022, [Peer-reviewed]
English, Scientific journal

A near-infrared fluorescent long-chain fatty acid toward optical imaging of cardiac metabolism in living mice
Mahadeva M. M. Swamy, Mohamad Zarif Mohd Zubir, Mutmainah, Setsuko Tsuboi, Yuta Murai, Kenji Monde, Ken-ichi Hirano, Takashi Jin
The Analyst, 147, 19, 4206, 4212, Royal Society of Chemistry (RSC), 2022, [Peer-reviewed]
English, Scientific journal, A near infrared fluorescence labelled long-chain fatty acid (FFA), Alexa680-BMPP (BMPP: 15-(4-(3-aminopropyl)phenyl)-3-methyl pentadecanoic acid), was synthesized as a fluorescent probe toward optical imaging of cardiac metabolism.

Shortwave-infrared (SWIR) emitting annexin V for high-contrast fluorescence molecular imaging of tumor apoptosis in living mice
Mahadeva M. M. Swamy, Setsuko Tsuboi, Yuta Murai, Kenji Monde, Takashi Jin
RSC Advances, 12, 30, 19632, 19639, Royal Society of Chemistry (RSC), 2022, [Peer-reviewed]
English, Scientific journal, The labelling of annexin V with indocyanine green (ICG) and π-conjugation extended ICG (ICG-C11) resulted in SWIR emitting probes that enable high-contrast molecular imaging of tumor apoptosis in living mice.

Stereostructural analysis of flexible oxidized fatty acids by VCD spectroscopy
Tohru Taniguchi, Naka Ida, Takuya Kitahara, Davidson Obinna Agbo, Kenji Monde
Chemical Communications, 58, 41, 6116, 6119, Royal Society of Chemistry (RSC), 2022, [Peer-reviewed]
English, Scientific journal, Using VCD spectroscopy to elucidate absolute configuration and conformational preferences of hydroxy fatty acids, lipid epoxides, and lipid hydroperoxides.

Deuterium labelling to extract local stereochemical information by VCD spectroscopy in the C–D stretching region: a case study of sugars
Mohamad Zarif Mohd Zubir, Nurul Fajry Maulida, Yoshihiro Abe, Yuta Nakamura, Mariam Abdelrasoul, Tohru Taniguchi, Kenji Monde
Organic & Biomolecular Chemistry, 20, 5, 1067, 1072, Royal Society of Chemistry (RSC), 2022, [Peer-reviewed]
English, Scientific journal, Methoxy-d₃ group installed at the C-1 position of a series of epimeric pairs of sugars generated mirror-image VCD patterns in the 2300–1900 cm⁻¹ region depending on the C-1 stereochemistry irrespective of the configurations at other positions.

Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether‐mediated Domino Reaction
Nariyoshi Umekubo, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi
Asian Journal of Organic Chemistry, 10, 12, 3261, 3265, Wiley, Dec. 2021, [Peer-reviewed], [International Magazine]
English, Scientific journal

Exploration of chromophores for a VCD couplet in a spectrally transparent infrared region for biomolecules
Tohru Taniguchi, Mohamad Zarif Mohd Zubir, Nobuyuki Harada, Kenji Monde
Physical Chemistry Chemical Physics, 23, 48, 27525, 27532, Royal Society of Chemistry (RSC), Nov. 2021, [Peer-reviewed]
English, Scientific journal, Introduction of chromophores in the 2300–2000 cm⁻¹ region such as nitrile and azido groups yields strong VCD signals whose shapes are indicative of molecular structures, as studied by experimental work and theoretical calculations.

Enantiodivergent One‐Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst‐Mediated Enantioselective Domino Reaction and Central‐to‐Axial Chirality Conversion
Seitaro Koshino, Tohru Taniguchi, Kenji Monde, Eunsang Kwon, Yujiro Hayashi
Chemistry – A European Journal, 27, 63, 15786, 15794, Wiley, Nov. 2021, [Peer-reviewed], [International Magazine]
English, Scientific journal

Shortwave-Infrared Fluorescent Molecular Imaging Probes Based on π-Conjugation Extended Indocyanine Green
Mahadeva M. M. Swamy, Yuta Murai, Kenji Monde, Setsuko Tsuboi, Takashi Jin
Bioconjugate Chemistry, 32, 8, 1541, 1547, American Chemical Society (ACS), 18 Aug. 2021, [Peer-reviewed], [International Magazine]
English, Scientific journal, Recently, shortwave-infrared (SWIR) fluorescence imaging for the optical diagnostics of diseases has attracted much attention as a new noninvasive imaging modality. For this application, the development of SWIR molecular imaging probes with high biocompatibility is crucial. Although many types of biocompatible SWIR fluorescent probes based on organic dyes have been reported, there are no SWIR-emitting molecular imaging probes that can be used for the detection of specific biomolecules in vivo. To apply SWIR-emitting molecular imaging probes to biomedical fields, we developed a biocompatible SWIR fluorescent dye based on π-conjugation extended indocyanine green (ICG), where ICG is the only approved near-infrared dye by the US Food and Drug Administration (FDA) for use in the clinic. Using the π-conjugation extended ICG, we prepared SWIR molecular imaging probes that can be used for in vivo tumor imaging. Herein, we demonstrate noninvasive SWIR fluorescence imaging of human epidermal growth factor receptor 2 (HER2)-positive and epidermal growth factor receptor (EGFR)-positive breast tumors using π-conjugation extended ICG and monoclonal antibody conjugates. The presented π-conjugation extended ICG analog probes will be a breakthrough to apply SWIR fluorescence imaging in biomedical fields.

こんにゃく由来グルコシルセラミド摂取による脳内アミロイドβ蓄積に対する抑制効果の探索的試験－プラセボ対照ランダム化二重盲検並行群間比較試験－　　　　　　　　　　　　　　　
江口 晃一, 向井 克之, 湯山 耕平, 栗本 成敬, 田中 藍子, 勝山(鏡) 豊代, 西平 順, 門出 健次, 五十嵐 靖之
薬理と治療, 49, 8, 1225, 1239, 2021, [Peer-reviewed]
Japanese, Scientific journal

Daurichromenic Acid from the Chinese Traditional Medicinal Plant Rhododendron dauricum Inhibits Sphingomyelin Synthase and Aβ Aggregation
Hadya Virupaksha Deepak, Mahadeva M. M. Swamy, Yuta Murai, Yoshiko Suga, Masaki Anetai, Takuro Yo, Masahiro Kuragano, Koji Uwai, Kiyotaka Tokuraku, Kenji Monde
Molecules, 25, 18, 4077, 4088, MDPI AG, Sep. 2020, [Peer-reviewed]
English, Scientific journal, Species of the genus Rhododendron have been used in traditional Chinese medicine, with the medicinal herb “Manshanfong” used as an expectorant and for the treatment of acute bronchitis. Daurichromenic acid (DCA), a constituent of Rhododendron dauricum, is a meroterpenoid with antibacterial, anti-HIV, and anti-inflammatory activities. However, the mechanisms underlying these pharmacologic activities are poorly understood. To develop new drugs based on DCA, more information is required regarding its interactions with biomolecules. The present study showed that DCA inhibits the activity of the enzyme sphingomyelin synthase, with an IC50 of 4 µM. The structure–activity relationships between DCA and sphingomyelin synthase were evaluated using derivatives and cyclized hongoquercin A. In addition, DCA was found to inhibit amyloid β aggregation. These results may help in the design of effective drugs based on DCA.

Inversion of the Axial Information during Oxidative Aromatization in the Synthesis of Axially Chiral Biaryls with Organocatalysis as a Key Step
Seitaro Koshino, Akira Takikawa, Keiichi Ishida, Tohru Taniguchi, Kenji Monde, Eunsang Kwon, Shigenobu Umemiya, Yujiro Hayashi
Chemistry – A European Journal, 26, 20, 4524, 4530, Wiley, 06 Apr. 2020, [Peer-reviewed]
English, Scientific journal

Effect of circularly polarized light on germination, hypocotyl elongation and biomass production of arabidopsis and lettuce: Involvement of phytochrome B
Enkhsukh Lkhamkhuu, Kazunori Zikihara, Hitomi Katsura, Satoru Tokutomi, Takafumi Hosokawa, Yoshihisa Usami, Mitsuyoshi Ichihashi, Junji Yamaguchi, Kenji Monde
Plant Biotechnology, 37, 1, 57, 67, Japanese Society for Plant Cell and Molecular Biology, 25 Mar. 2020, [Peer-reviewed], [Domestic magazines]
English, Scientific journal, Circular dichroism (CD), defined as the differential absorption of left- and right-handed circularly polarized light (CPL), is a useful spectroscopic technique for structural studies of biological systems composed of chiral molecules. The present study evaluated the effects of CPL on germination, hypocotyl elongation and biomass production of Arabidopsis and lettuce. Higher germination rates were observed when Arabidopsis and lettuce seedlings were irradiated with red right-handed CPL (R-CPL) than with red left-handed CPL (L-CPL). Hypocotyl elongation was effectively inhibited when Arabidopsis and lettuce seedlings were irradiated with red R-CPL than with red L-CPL. This difference was not observed when a phytochrome B (phyB) deficient mutant of Arabidopsis was irradiated, suggesting that inhibition of elongation by red R-CPL was mediated by phyB. White R-CPL induced greater biomass production by adult Arabidopsis plants, as determined by their fresh shoot weight, than white L-CPL. To determine the molecular basis of these CPL effects, CD spectra and the effect of CPL on the photoreaction of a sensory module of Arabidopsis phyB were measured. The red light-absorbing form of phyB showed a negative CD in the red light-absorbing region, consistent with the results of germination, inhibition of hypocotyl elongation and biomass production. L-CPL and R-CPL, however, did not differ in their ability to induce the interconversion of the red light-absorbing and far-red light-absorbing forms of phyB. These findings suggest that these CPL effects involve phyB, along with other photoreceptors and the photosynthetic process.

Chiral combinatorial preparation and biological evaluation of unique ceramides for inhibition of sphingomyelin synthase.
Sajeer Koolath, Yuta Murai, Yoshiko Suga, Kenji Monde
Chirality, 32, 3, 308, 313, Mar. 2020, [Peer-reviewed], [International Magazine]
English, Scientific journal, Enantiomers or diastereomers of chiral bioactive compounds often exhibit different biological and toxicological properties. Here, we report the efficient synthesis of four stereoisomers of sphingosine and derivatization of unique chiral ceramides through a combinatorial chemistry by solid-phase activated resin ester. In addition, to test the effectivity of stereochemistry of ceramide, we demonstrated a cell-based assay of sphingomyelin synthase inhibition in the presence ofchiral unique ceramides, which suggested that libraries of this sort will be a rich source of biologically active synthetic molecules.

Nrp1 is Activated by Konjac Ceramide Binding-Induced Structural Rigidification of the a1a2 Domain.
Seigo Usuki, Yoshiaki Yasutake, Noriko Tamura, Tomohiro Tamura, Kunikazu Tanji, Takashi Saitoh, Yuta Murai, Daisuke Mikami, Kohei Yuyama, Kenji Monde, Katsuyuki Mukai, Yasuyuki Igarashi
Cells, 9, 2, 24 Feb. 2020, [Peer-reviewed], [International Magazine]
English, Scientific journal, Konjac ceramide (kCer) is a plant-type ceramide composed of various long-chain bases and a-hydroxyl fatty acids. The presence of d4t,8t-sphingadienine is essential for semaphorin 3A (Sema3A)-like activity. Herein, we examined the three neuropilin 1 (Nrp1) domains (a1a2, b1b2, or c), and found that a1a2 binds to d4t,8t-kCer and possesses Sema3A-like activity. kCer binds to Nrp1 with a weak affinity of mM dissociation constant (Kd). We wondered whether bovine serum albumin could influence the ligand-receptor interaction that a1a2 has with a single high affinity binding site for kCer (Kd in nM range). In the present study we demonstrated the influence of bovine serum albumin. Thermal denaturation indicates that the a1a2 domain may include intrinsically disordered region (IDR)-like flexibility. A potential interaction site on the a1 module was explored by molecular docking, which revealed a possible Nrp1 activation mechanism, in which kCer binds to Site A close to the Sema3A-binding region of the a1a2 domain. The a1 module then accesses a2 as the IDR-like flexibility becomes ordered via kCer-induced protein rigidity of a1a2. This induces intramolecular interaction between a1 and a2 through a slight change in protein secondary structure.

Design and Synthesis of Ligand‐Tag Exchangeable Photoaffinity Probe Utilizing Nosyl Chemistry
Saaidin S. A., Murai, Y., Ishikawa, T., Monde, K.
Eur. J. Org. Chem., 2019, 46, 7563, 7567, Dec. 2019, [Peer-reviewed]
English, Scientific journal

Malabaricone C as Natural Sphingomyelin Synthase Inhibitor against Diet-Induced Obesity and Its Lipid Metabolism in Mice.
Muhamad Aqmal Othman, Kohei Yuyama, Yuta Murai, Yasuyuki Igarashi, Daisuke Mikami, Yasodha Sivasothy, Khalijah Awang, Kenji Monde
ACS medicinal chemistry letters, 10, 8, 1154, 1158, 08 Aug. 2019, [Peer-reviewed], ［Internationally co-authored］, [International Magazine]
English, Scientific journal, The interaction between natural occurring inhibitors and targeted membrane proteins could be an alternative medicinal strategy for the treatment of metabolic syndrome, notably, obesity. In this study, we identified malabaricones A-C and E (1-4) isolated from the fruits of Myristica cinnamomea King as natural inhibitors for sphingomyelin synthase (SMS), a membrane protein responsible for sphingolipid biosynthesis. Having the most promising inhibition, oral administration of compound 3 exhibited multiple efficacies in reducing weight gain, improving glucose tolerance, and reducing hepatic steatosis in high fat diet-induced obesity mice models. Liver lipid analysis revealed a crucial link between the SMS activities of compound 3 and its lipid metabolism in vitro and in vivo. The nontoxic nature of compound 3 makes it a suitable candidate in search of drugs which can be employed in the treatment and prevention of obesity.

First enantioselective synthesis of salinipostin A, a marine cyclic enol-phosphotriester isolated from Salinispora sp
Hironori Okamura, Takanobu Fujioka, Naoki Mori, Tohru Taniguchi, Kenji Monde, Hidenori Watanabe, Hirosato Takikawa
Tetrahedron Letters, 60, 32, 150917, 150917, Elsevier BV, Aug. 2019, [Peer-reviewed]
English, Scientific journal

An automated microliter-scale high-throughput screening system (MSHTS) for real-time monitoring of protein aggregation using quantum-dot nanoprobes.
Rina Sasaki, Reina Tainaka, Yuichi Ando, Yurika Hashi, Hadya V Deepak, Yoshiko Suga, Yuta Murai, Masaki Anetai, Kenji Monde, Kiminori Ohta, Ikuko Ito, Haruhisa Kikuchi, Yoshiteru Oshima, Yasuyuki Endo, Hitomi Nakao, Masafumi Sakono, Koji Uwai, Kiyotaka Tokuraku
Scientific reports, 9, 1, 2587, 2587, Feb. 2019, [Peer-reviewed], [International Magazine]
English, Scientific journal, Protein aggregation is the principal component of numerous protein misfolding pathologies termed proteinopathies, such as Alzheimer's disease, Parkinson's disease, prion disease, and AA amyloidosis with unmet treatment needs. Protein aggregation inhibitors have great potential for the prevention and treatment of proteinopathies. Here we report the development of an automated real-time microliter-scale high throughput screening (MSHTS) system for amyloid aggregation inhibitors using quantum-dot nanoprobes. Screening 504 crude extracts and 134 low molecular weight aromatic compounds revealed the relationship of amyloid-β (Aβ) aggregation inhibitory activities of plant extracts using a plant-based classification. Within the eudicots, rosids, Geraniales and Myrtales showed higher activity. Screening low molecular weight aromatic compounds demonstrated that the structure of tropolone endows it with potential Aβ aggregation inhibitory activity. The activity of the most active tropolone derivative was higher than that of rosmarinic acid. MSHTS also identified three chaperone molecules as tau aggregation inhibitors. These results demonstrate that our automated MSHTS system is a novel and robust tool that can be adapted to a wide range of compounds and aggregation-prone polypeptides.

Determination of the Absolute Configurations and the Sensory Properties of the Enantiomers of a Homologous Series (C6–C10) of 2-Mercapto-4-alkanones
Kiske, C, Riegel, A, Hopf, R, Kvindt, A, Poplacean, I, Taniguchi, T, Swamy, M, Monde, K, Eisenreich, W, Engel, K
J. Agric. Food Chem., 67, 4, 1187, 1196, Jan. 2019, [Peer-reviewed], ［Internationally co-authored］
English, Scientific journal

Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor.
Mahadeva M M Swamy, Yuta Murai, Yusuke Ohno, Keisuke Jojima, Akio Kihara, Susumu Mitsutake, Yasuyuki Igarashi, Jian Yu, Min Yao, Yoshiko Suga, Masaki Anetai, Kenji Monde
Chemical communications (Cambridge, England), 54, 90, 12758, 12761, 08 Nov. 2018, [Peer-reviewed], [International Magazine]
English, Scientific journal, Ginkgolic acid obtained as a sphingomyelin synthase inhibitor from a plant extract library inspired the concept of sphingolipid mimics. Ginkgolic acid-derived N-acyl anilines and ginkgolic acid 2-phosphate (GA2P) respectively mimic ceramide and sphingosine 1-phosphate (S1P) in structure and function. The GA2P-induced phosphorylation of ERK and internalization of S1P receptor 1 (S1P1) indicated potent agonist activity. Docking studies revealed that GA2P adopts a similar binding conformation to the bound ligand ML5, which is a strong antagonist of S1P1.

Preparation of Carbodiimides with One-Handed Axial Chirality
Taniguchi, T, Suzuki, T, Satoh, H, Shichibu, Y, Konishi, K, Monde, K
J. Am. Chem. Soc., 140, 46, 15577, 15581, Nov. 2018, [Peer-reviewed]
English, Scientific journal

Synthesis and Photochemical Properties of Axially Chiral Bis(dinaphthofuran)
Katakami, C, Kamo, S, Torii, A, Hara, N, Imai, Y, Taniguchi, T, Monde, K, Okabayashi, Y, Hosokai, T, Kuramochi, K, Tsubaki, K
J. Org. Chem., 83, 23, 14610, 14616, Oct. 2018, [Peer-reviewed]
English, Scientific journal

Palladium-Catalyzed Asymmetric C(sp³)-H Allylation of 2-Alkylpyridines
Murakami R, Sano K, Iwai T, Taniguchi T, Monde K, Sawamura M
Angew. Chem., Int. Ed., 57, 30, 9465, 9469, Jul. 2018, [Peer-reviewed]
English, Scientific journal

Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst
Genki Kawauchi, Shigenobu Umemiya, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi
Chemistry - A European Journal, 24, 33, 8409, 8414, Wiley-VCH Verlag, 12 Jun. 2018, [Peer-reviewed]
English, Scientific journal

Modifying oligoalanine conformation by replacement of amide to ester linkage
Takahiro Hongen, Tohru Taniguchi, Kenji Monde
Chirality, 30, 4, 396, 401, John Wiley and Sons Inc., 01 Apr. 2018, [Peer-reviewed]
English, Scientific journal

Stereochemistry (and Conformation) of Nucleosides and Their Synthetic Precursors by Vibrational Circular Dichroism
Taniguchi, T, Nakano, K, Monde, K
Current Protocols in Nucleic Acid Chemistry, 72, 1, 7.29.1, 7.29.9, Mar. 2018, [Peer-reviewed]
English, Scientific journal

Facile Chemoselective Strategy toward Capturing Sphingoid Bases by a Unique Glutaraldehyde-Functionalized Resin.
Siddabasave Gowda B Gowda, Atsufumi Nakahashi, Keiko Yamane, Saori Nakahashi, Yuta Murai, Ananda Kumar C Siddegowda, Mostafa A S Hammam, Kenji Monde
ACS omega, 3, 1, 753, 759, 31 Jan. 2018, [Peer-reviewed], [International Magazine]
English, Scientific journal, Sphingoid bases, which have a 2-amino-1,3-diol common functional group, are the structural backbone units of all sphingolipids. Recently, much attention has been focused on sphingoid bases because of their potentially beneficial bioactivities toward various cancer cells as well as their dietary interest. However, low abundance and the handling complexity caused by their amphiphilic character led to very limited research on them. Glutaraldehyde has two aldehyde groups, and it reacts rapidly with the 2-amino-1,3-diol functional group of sphingosine to give a tricyclic product. Immobilization of glutaraldehyde on a resin was successfully performed by organic synthesis, starting from trans-p-coumaric acid via eight steps. This approach suppresses the self-polymerization of glutaraldehyde, and addition of water to the developed resin causes the formation of cyclic double hemiacetal function, which avoids oxidation like a reducing sugar in nature and makes it stable even for up to 1 year incubation. The resin was applied to the solid-phase extracting experiment of free sphingosine from human serum at a concentration of 280 nM. Another extraction study of edible golden oyster mushrooms showed that the sphingoid base was selectively captured from complex natural extracts. These results demonstrate that the developed glutaraldehyde resin method is a highly selective method, and hence, the combination of it with the o-phthaldialdehyde HPLC method was confirmed as an efficient and sensitive method for analysis of sphingoid bases in biological samples.

Focused Genome Mining of Structurally Related Sesterterpenes: Enzymatic Formation of Enantiomeric and Diastereomeric Products
Koji Narita, Hajime Sato, Atsushi Minami, Kosei Kudo, Lei Gao, Chengwei Liu, Taro Ozaki, Motoichiro Kodama, Xiaoguang Lei, Tohru Taniguchi, Kenji Monde, Mami Yamazaki, Masanobu Uchiyama, Hideaki Oikawa
ORGANIC LETTERS, 19, 24, 6696, 6699, Dec. 2017, [Peer-reviewed]
English, Scientific journal

Asymmetric Synthesis of beta-Lactams through Copper-Catalyzed Alkyne-Nitrone Coupling with a Prolinol-Phosphine Chiral Ligand
Yurie Takayama, Takaoki Ishii, Hirohisa Ohmiya, Tomohiro Iwai, Martin C. Schwarzer, Seiji Mori, Tohru Taniguchi, Kenji Monde, Masaya Sawamura
CHEMISTRY-A EUROPEAN JOURNAL, 23, 35, 8400, 8404, Jun. 2017, [Peer-reviewed]
English, Scientific journal

Formal (4+1) Cycloaddition and Enantioselective Michael-Henry Cascade Reactions To Synthesize Spiro[4,5]decanes and Spirooxindole Polycycles
Ji-Rong Huang, Muhammad Sohail, Tohru Taniguchi, Kenji Monde, Fujie Tanaka
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56, 21, 5853, 5857, May 2017, [Peer-reviewed]
English, Scientific journal

Synthesis of Nontoxic Fluorous Sphingolipids as Molecular Probes of Exogenous Metabolic Studies for Rapid Enrichment by Fluorous Solid Phase Extraction
Shota Saito, Yuta Murai, Seigo Usuki, Masafumi Yoshida, Mostafa A. S. Hammam, Susumu Mitsutake, Kohei Yuyama, Yasuyuki Igarashi, Kenji Monde
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6, 1045, 1051, Feb. 2017, [Peer-reviewed]
English, Scientific journal

化学プローブは求愛タンパク質の心をどう射留めるのか？-生命現象解明・創薬に小分子の視点から　　　　　　　　　　　　　　　
門出 健次, 村井 勇太
化学, 72, 10, 70, 71, 2017
Japanese

Practical Use of Circular Dichroism and Vibrational Circular Dichroism for Structural Analysis
Tohru Taniguchi, Kenji Monde
Journal of Synthetic Organic Chemistry, Japan, 75, 5, 522, 529, 2017
Japanese, Scientific journal

Analysis of Configuration and Conformation of Furanose Ring in Carbohydrate and Nucleoside by Vibrational Circular Dichroism
Tohru Taniguchi, Kie Nakano, Ryosuke Baba, Kenji Monde
ORGANIC LETTERS, 19, 2, 404, 407, Jan. 2017, [Peer-reviewed]
English, Scientific journal

alpha-Arylation of alpha-Amino Acid Derivatives with Arynes via Memory of Chirality: Asymmetric Synthesis of Benzocyclobutenones with Tetrasubstituted Carbon
Koji Kasamatsu, Tomoyuki Yoshimura, Attila Mandi, Tohru Taniguchi, Kenji Monde, Takumi Furuta, Takeo Kawabata
ORGANIC LETTERS, 19, 2, 352, 355, Jan. 2017, [Peer-reviewed]
English, Scientific journal

Reinvestigation of the Absolute Configurations of Chiral beta-Mercaptoalkanones Using Vibrational Circular Dichroism and H-1 NMR Analysis
Christiane Kiske, Svenja Noerenberg, Miriam Ecker, Xingyue Ma, Tohru Taniguchi, Kenji Monde, Wolfgang Eisenreich, Karl-Heinz Engel
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 64, 45, 8563, 8571, Nov. 2016, [Peer-reviewed]
English, Scientific journal

Asymmetric Diels-Alder Reaction of -Substituted and ,-Disubstituted ,-Enals via Diarylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereocenters
Yujiro Hayashi, Bojan P. Bondzic, Tatsuya Yamazaki, Yogesh Gupta, Shin Ogasawara, Tohru Taniguchi, Kenji Monde
CHEMISTRY-A EUROPEAN JOURNAL, 22, 44, 15874, 15880, Oct. 2016, [Peer-reviewed]
English, Scientific journal

Studying the stereostructures of biomolecules and their analogs by vibrational circular dichroism
Tohru Taniguchi, Takahiro Hongen, Kenji Monde
POLYMER JOURNAL, 48, 9, 925, 931, Sep. 2016, [Peer-reviewed], [Invited]
English, Scientific journal

A Bioinspired Synthesis of (+/-)-Rubrobramide, (+/-)-Flavipucine, and (+/-)-Isoflavipucine
Shoma Mizutani, Kenta Komori, Tohru Taniguchi, Kenji Monde, Kouji Kuramochi, Kazunori Tsubaki
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 55, 33, 9553, 9556, Aug. 2016, [Peer-reviewed]
English, Scientific journal

Facile Diastereoseparation of Glycosyl Sulfoxides by Chiral Stationary Phase
Tohru Taniguchi, Mai Asahata, Akihito Nasu, Yukatsu Shichibu, Katsuaki Konishi, Kenji Monde
CHIRALITY, 28, 7, 534, 539, Jul. 2016, [Peer-reviewed]
English, Scientific journal

Reducing Molecular Flexibility by Cyclization for Elucidation of Absolute Configuration by CD Calculations: Daurichromenic Acid
Attila Mandi, Mahadeva M. M. Swamy, Tohru Taniguchi, Masaki Anetai, Kenji Monde
CHIRALITY, 28, 6, 453, 459, Jun. 2016, [Peer-reviewed]
English, Scientific journal

Stereochemical Study of Sphingosine by Vibrational Circular Dichroism
Atsufumi Nakahashi, Ananda Kumar C. Siddegowda, Mostafa A. S. Hammam, Siddabasave Gowda B. Gowda, Yuta Murai, Kenji Monde
ORGANIC LETTERS, 18, 10, 2327, 2330, May 2016, [Peer-reviewed]
English, Scientific journal

Efficient Synthesis of Photoreactive 2-Propoxyaniline Derivatives as Artificial Sweeteners
Yuta Murai, Takuma Yoshida, Lei Wang, Katsuyoshi Masuda, Yasuyuki Hashidoko, Kenji Monde, Yasumaru Hatanaka, Makoto Hashimoto
SYNLETT, 27, 6, 946, 950, Apr. 2016, [Peer-reviewed]
English, Scientific journal

Enantioselective Synthesis of Aminoindan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino-Acid-Tethered Triynes
Yu-ki Tahara, Shuhei Obinata, Kyalo Stephen Kanyiva, Takanori Shibata, Attila Mandi, Tohru Taniguchi, Kenji Monde
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 7, 1405, 1413, Mar. 2016, [Peer-reviewed]
English, Scientific journal

What Is the True Structure of D609, a Widely Used Lipid Related Enzyme Inhibitor?
Mikako Kato, Mostafa A. S. Hammam, Tohru Taniguchi, Yoshiko Suga, Kenji Monde
ORGANIC LETTERS, 18, 4, 768, 771, Feb. 2016, [Peer-reviewed]
English, Scientific journal

Stereochemistry of a Rhododaurichromanic Acid Derivative
Mahadeva M. M. Swamy, Attila Mandi, Masaki Anetai, Kenji Monde
NATURAL PRODUCT COMMUNICATIONS, 11, 2, 193, 195, Feb. 2016, [Peer-reviewed]
English, Scientific journal

Highly efficient preparation of sphingoid bases from glucosylceramides by chemoenzymatic method
Siddabasave B. Gowda Gowda, Seigo Usuki, Mostafa A. S. Hammam, Yuta Murai, Yasuyuki Igarashi, Kenji Monde
JOURNAL OF LIPID RESEARCH, 57, 2, 325, 331, Feb. 2016, [Peer-reviewed]
English, Scientific journal

VCD exciton chirality method
門出 健次, 谷口 透
分光研究, 65, 2, 137, 144, 日本分光学会, 2016
Japanese

Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide - detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy
Siyuan Wang, Tohru Taniguchi, Kenji Monde, Masatoshi Kawahata, Kentaro Yamaguchi, Yuko Otani, Tomohiko Ohwada
CHEMICAL COMMUNICATIONS, 52, 21, 4018, 4021, 2016, [Peer-reviewed]
English, Scientific journal

Epigenetic stimulation of polyketide production in Chaetomium cancroideum by an NAD(+)-dependent HDAC inhibitor
Teigo Asai, Shuntaro Morita, Tohru Taniguchi, Kenji Monde, Yoshiteru Oshima
ORGANIC & BIOMOLECULAR CHEMISTRY, 14, 2, 646, 651, 2016, [Peer-reviewed]
English, Scientific journal

Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism
Tohru Taniguchi, Daisuke Manai, Masataka Shibata, Yutaka Itabashi, Kenji Monde
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 137, 38, 12191, 12194, Sep. 2015, [Peer-reviewed]
English, Scientific journal

Genome Mining for Sesterterpenes Using Bifunctional Terpene Synthases Reveals a Unified Intermediate of Di/Sesterterpenes
Ying Ye, Atsushi Minami, Attila Mandi, Chengwei Liu, Tohru Taniguchi, Tomohisa Kuzuyama, Kenji Monde, Katsuya Gomi, Hideaki Oikawa
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 137, 36, 11846, 11853, Sep. 2015, [Peer-reviewed]
English, Scientific journal

Asymmetric Nitrocyclopropanation of alpha-Substituted alpha,beta-Enals Catalyzed by Diphenylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereogenic Centers
Yujiro Hayashi, Tatsuya Yamazaki, Yuki Nakanishi, Tsuyoshi Ono, Tohru Taniguchi, Kenji Monde, Tadafumi Uchimaru
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 26, 5747, 5754, Sep. 2015, [Peer-reviewed]
English, Scientific journal

Vibrational CD (VCD) Spectroscopy as a Powerful Tool for Chiral Analysis of Flavor Compounds
Yoshihiro Yaguchi, Atsufumi Nakahashi, Nobuaki Miura, Tohru Taniguchi, Daisuke Sugimoto, Makoto Emura, Kyoko Zaizen, Yumi Kusano, Kenji Monde
IMPORTANCE OF CHIRALITY TO FLAVOR COMPOUNDS, 1212, 35, 56, 2015, [Peer-reviewed]
English, International conference proceedings

Revision of the relative and absolute stereochemistries of 3-hydroxydehydroiso-alpha-lapachone and its 8-hydroxy derivative
Poonam Khandelwal, Pahup Singh, Tohru Taniguchi, Kenji Monde, Kohei Johmoto, Hidehiro Uekusa, Hironori Masubuti, Yoshinori Fujimoto
PHYTOCHEMISTRY LETTERS, 10, 224, 229, Dec. 2014, [Peer-reviewed]
English, Scientific journal

Stereoselective synthesis of 1-methoxyspiroindoline phytoalexins and their amino analogues
Aneta Salayova, Zuzana Kudlickova, Matej Balaz, Mariana Budovska, Martina Pilatova, Jan Mojzis, Kenji Monde, Jan Petrovaj, Tatana Gondova
TETRAHEDRON-ASYMMETRY, 25, 16-17, 1221, 1233, Sep. 2014, [Peer-reviewed]
English, Scientific journal

In Depth Study on Solution-State Structure of Poly(lactic acid) by Vibrational Circular Dichroism
Takahiro Hongen, Tohru Taniguchi, Shintaro Nomura, Jun-ichi Kadokawa, Kenji Monde
MACROMOLECULES, 47, 15, 5313, 5319, Aug. 2014, [Peer-reviewed]
English, Scientific journal

ENANTIOSELECTIVE INTRAMOLECULAR AZA-SPIROANNULATION ONTO BENZOFURANS USING CHIRAL RHODIUM CATALYSIS
Takuro Shibuta, Shigeki Sato, Masatoshi Shibuya, Naoki Kanoh, Tohru Taniguchi, Kenji Monde, Yoshiharu Iwabuchi
HETEROCYCLES, 89, 3, 631, 639, Mar. 2014, [Peer-reviewed]
English, Scientific journal

Short Synthesis of Berkeleyamide D and Determination of the Absolute Configuration by the Vibrational Circular Dichroism Exciton Chirality Method
Kenta Komori, Tohru Taniguchi, Shoma Mizutani, Kenji Monde, Kouji Kuramochi, Kazunori Tsubaki
ORGANIC LETTERS, 16, 5, 1386, 1389, Mar. 2014, [Peer-reviewed]
English, Scientific journal

Structures of Spiroindicumides A and B, Unprecedented Carbon Skeletal Spirolactones, and Determination of the Absolute Configuration by Vibrational Circular Dichroism Exciton Approach
Teigo Asai, Tohru Taniguchi, Takashi Yamamoto, Kenji Monde, Yoshiteru Oshima
ORGANIC LETTERS, 15, 17, 4320, 4323, Sep. 2013, [Peer-reviewed]
English, Scientific journal

Structurally Diverse Chaetophenol Productions Induced by Chemically Mediated Epigenetic Manipulation of Fungal Gene Expression
Teigo Asai, Takashi Yamamoto, Naoki Shirata, Tohru Taniguchi, Kenji Monde, Isao Fujii, Katsuya Gomi, Yoshiteru Oshima
ORGANIC LETTERS, 15, 13, 3346, 3349, Jul. 2013, [Peer-reviewed]
English, Scientific journal

Structures and absolute configurations of short-branched fatty acid dimers from an endophytic fungus of Aloe arborescens
Teigo Asai, Sae Otsuki, Tohru Taniguchi, Kenji Monde, Kouwa Yamashita, Hiroaki Sakurai, Tomoji Ozeki, Yoshiteru Oshima
TETRAHEDRON LETTERS, 54, 26, 3402, 3405, Jun. 2013, [Peer-reviewed]
English, Scientific journal

糸状菌二次代謝を活性化するNAD依存型HDAC阻害剤の探索とそれを用いた新規天然物の創出　　　　　　　　　　　　　　　
森田 峻太郎, 浅井 禎吾, 谷口 透, 門出 健次, 櫻井 博章, 尾関 智二, 山下 幸和, 大島 吉輝
日本薬学会年会要旨集, 133年会, 2, 177, 177, (公社)日本薬学会, Mar. 2013, [Peer-reviewed]
Japanese

Structural Diversity of New C-13-Polyketides Produced by Chaetomium mollipilium Cultivated in the Presence of a NAD(+)-Dependent Histone Deacetylase Inhibitor
Teigo Asai, Shuntaro Morita, Naoki Shirata, Tohru Taniguchi, Kenji Monde, Hiroaki Sakurai, Tomoji Ozeki, Yoshiteru Oshima
ORGANIC LETTERS, 14, 21, 5456, 5459, Nov. 2012, [Peer-reviewed]
English, Scientific journal

Dihydrobenzofurans as cannabinoid receptor ligands from Cordyceps annullata, an entomopathogenic fungus cultivated in the presence of an HDAC inhibitor
Teigo Asai, Dan Luo, Yutaro Obara, Tohru Taniguchi, Kenji Monde, Kouwa Yamashita, Yoshiteru Oshima
TETRAHEDRON LETTERS, 53, 17, 2239, 2243, Apr. 2012, [Peer-reviewed]
English, Scientific journal

Enantioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition
Takanori Shibata, Mayu Miyoshi, Toshifumi Uchiyama, Kohei Endo, Nobuaki Miura, Kenji Monde
TETRAHEDRON, 68, 12, 2679, 2686, Mar. 2012, [Peer-reviewed]
English, Scientific journal

Optical Rotation, Electronic Circular Dichroism, and Vibrational Circular Dichroism of Carbohydrates and Glycoconjugates
Tohru Taniguchi, Kenji Monde
Comprehensive Chiroptical Spectroscopy, 2, 795, 818, John Wiley and Sons, 17 Feb. 2012, [Peer-reviewed]
English, In book

Exciton Chirality Method in Vibrational Circular Dichroism
Tohru Taniguchi, Kenji Monde
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 134, 8, 3695, 3698, Feb. 2012, [Peer-reviewed]
English, Scientific journal

Salvileucalin C, a novel rearranged neoclerodane diterpene from Salvia leucantha
Yutaka Aoyagi, Akira Yamazaki, Reiko Kato, Fukuya Tobe, Haruhiko Fukaya, Tadateru Nishikawa, Atsufumi Nakahashi, Nobuaki Miura, Kenji Monde, Koichi Takeya
TETRAHEDRON LETTERS, 52, 16, 1851, 1853, Apr. 2011, [Peer-reviewed]
English, Scientific journal

A Vibrational Circular Dichroism Approach to the Determination of the Absolute Configurations of Flavorous 5-Substituted-2(5H)-furanones
Atsufumi Nakahashi, Yoshihiro Yaguchi, Nobuaki Miura, Makoto Emura, Kenji Monde
JOURNAL OF NATURAL PRODUCTS, 74, 4, 707, 711, Apr. 2011, [Peer-reviewed]
English, Scientific journal

(R)-(+)-[VCD(-)984]-4-Ethyl-4-methyloctane: A Cryptochiral Hydrocarbon with a Quaternary Chiral Center. (1) Synthesis of the Enantiopure Compound and Unambiguous Determination of Absolute Configuration
Takuma Fujita, Kazuhiro Obata, Shunsuke Kuwahara, Atsufumi Nakahashi, Kenji Monde, John Decatur, Nobuyuki Harada
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 33, 33, 6372, 6384, Nov. 2010, [Peer-reviewed]
English, Scientific journal

(R)-(+)-[VCD(-)984]-4-Ethyl-4-methyloctane: A Cryptochiral Hydrocarbon with a Quaternary Chiral Center. (2) Vibrational CD Spectra of Both Enantiomers and Absolute Configurational Assignment
Shunsuke Kuwahara, Kazuhiro Obata, Takuma Fujita, Nobuaki Miura, Atsufumi Nakahashi, Kenji Monde, Nobuyuki Harada
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 33, 33, 6385, 6392, Nov. 2010, [Peer-reviewed]
English, Scientific journal

Super water- and highly oil-repellent films made of fluorinated poly(alkylpyrroles)
Kaori Chiba, Kazutomo Kurogi, Kenji Monde, Mai Hashimoto, Masafumi Yoshida, Hiroyuki Mayama, Kaoru Tsujii
COLLOIDS AND SURFACES A-PHYSICOCHEMICAL AND ENGINEERING ASPECTS, 354, 1-3, 234, 239, Feb. 2010
English, Scientific journal

Stereochemical Studies of Odorous 2-Substituted-3(2H)-furanones by Vibrational Circular Dichroism
Makoto Emura, Yoshihiro Yaguchi, Atsufumi Nakahashi, Daisuke Sugimoto, Nobuaki Miura, Kenji Monde
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 57, 21, 9909, 9915, Nov. 2009, [Peer-reviewed]
English, Scientific journal

Stereochemical studies of hexylitaconic acid, an inhibitor of p53-HDM2 interaction
Atsufumi Nakahashi, Nobuaki Miura, Kenji Monde, Sachiko Tsukamoto
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 19, 11, 3027, 3030, Jun. 2009
English, Scientific journal

Vibrational CD spectroscopy as a powerful tool for stereochemical study of cyclophynes in solution
De Lie An, Qiang Chen, Jingkun Fang, Hong Yan, Akihiro Orita, Nobuaki Miura, Atsufumi Nakahashi, Kenji Monde, Junzo Otera
TETRAHEDRON LETTERS, 50, 15, 1689, 1692, Apr. 2009, [Peer-reviewed]
English, Scientific journal

Absolute Configuration of Actinophyllic Acid As Determined through Chiroptical Data
Tohru Taniguchi, Connor L. Martin, Kenji Monde, Koji Nakanishi, Nina Berova, Larry E. Overman
JOURNAL OF NATURAL PRODUCTS, 72, 3, 430, 432, Mar. 2009, [Peer-reviewed]
English, Scientific journal

Stereochemical Study of a Novel Tautomeric Furanone, Homofuraneol
Kenji Monde, Atsufumi Nakahashi, Nobuaki Miura, Yoshihiro Yaguchi, Daisuke Sugimoto, Makoto Emura
CHIRALITY, 21, 1E, E110, E115, 2009
English, Scientific journal

Alterations in the glycoform of cisplatin-resistant human carcinoma cells are caused by defects in the endoplasmic reticulum-associated degradation system
Hiroaki Nakagawa, Miki Ohira, Shunji Hayashi, Shigeaki Abe, Shin Saito, Noriko Nagahori, Kenji Monde, Yasuro Shinohara, Naoki Fujitani, Hirosato Kondo, Shin-Ichi Akiyama, Akira Nakagawara, Shin-Ichiro Nishimura
CANCER LETTERS, 270, 2, 295, 301, Nov. 2008
English, Scientific journal

Stereochemical Study of Chiral Tautomeric Flavorous Furanones by Vibrational Circular Dichroism
Yoshihiro Yaguchi, Atsufumi Nakahashi, Nobuaki Miura, Daisuke Sugimoto, Kenji Monde, Makoto Emura
ORGANIC LETTERS, 10, 21, 4883, 4885, Nov. 2008
English, Scientific journal

Observation and characterization of a specific vibrational circular dichroism band in phenyl glycosides
Tohru Taniguchi, Ikuko Tone, Kenji Monde
CHIRALITY, 20, 3-4, 446, 453, Mar. 2008
English, Scientific journal

Glycoconjugate Data Bank : Structures - an annotated glycan structure database and N-glycan primary structure verification service
Taku Nakahara, Ryo Hashimoto, Hiroaki Nakagawa, Kenji Monde, Nobuaki Miura, Shin-Ichiro Nishimura
NUCLEIC ACIDS RESEARCH, 36, D368, D371, Jan. 2008
English, Scientific journal

Chiral sulfinates studied by optical rotation, ECD and VCD: the absolute configuration of a cruciferous phytoalexin brassicanal C
Tohru Taniguchi, Kenji Monde, Koji Nakanishi, Nina Berova
ORGANIC & BIOMOLECULAR CHEMISTRY, 6, 23, 4399, 4405, 2008
English, Scientific journal

Stereoselective synthesis of (R)-(+)-1-methoxyspirobrassinin, (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether and their enantiomers or diastereoisomers
Zuzana C. Curillova, Peter Kutschy, Mariana Budovska, Atsufumi Nakahashi, Kenji Monde
TETRAHEDRON LETTERS, 48, 46, 8200, 8204, Nov. 2007
English, Scientific journal

Stereochemical studies of sialic acid derivatives by vibrational circular dichroism
Atsufumi Nakahashi, Tohru Taniguchi, Nobuaki Miura, Kenji Monde
ORGANIC LETTERS, 9, 23, 4741, 4744, Nov. 2007
English, Scientific journal

Spectrum–Structure Relationship in Carbohydrate Vibrational Circular Dichroism and Its Application to Glycoconjugates
Tohru Taniguchi, Kenji Monde
Chemistry – An Asian Journal, 2, 10, 1258, 1266, Oct. 2007, [Peer-reviewed]
English, Scientific journal

Effects of central metal ions on vibrational circular dichroism spectra of Tris-(beta-diketonato)metal(III) complexes
Hisako Sato, Tohru Taniguchi, Atsufumi Nakahashi, Kenji Monde, Akihiko Yamagishi
INORGANIC CHEMISTRY, 46, 16, 6755, 6766, Aug. 2007
English

A structure and an absolute configuration of (+)-alternamin, a new coumarin from Murraya alternans having antidote activity against snake venom
Hia Myoe Min, Mya Aye, Tohru Taniguchi, Nobuaki Miura, Kenji Monde, Kazuhiko Ohzawa, Toshiaki Nikai, Masatake Niwa, Yoshiaki Takaya
TETRAHEDRON LETTERS, 48, 35, 6155, 6158, Aug. 2007, [Peer-reviewed]
English, Scientific journal

Effect of pore size on in vitro cartilage formation using chitosan-based hyaluronic acid hybrid polymer fibers
Shintaro Yamane, Norimasa Iwasaki, Yasuhiko Kasahara, Kazuo Harada, Tokifumi Majima, Kenji Monde, Shin-ichiro Nishimura, Akio Minami
JOURNAL OF BIOMEDICAL MATERIALS RESEARCH PART A, 81A, 3, 586, 593, Jun. 2007
English, Scientific journal

(R)-(+)-[VCD(+)9451-4-ethyl-4-methyloctane, the simplest chiral saturated hydrocarbon with a quaternary stereogenic center
Takuma Fujita, Kazuhiro Obataa, Shunsuke Kuwahara, Nobuaki Miura, Atsufumi Nakahashi, Kenji Monde, John Decatur, Nobuyuki Harada
TETRAHEDRON LETTERS, 48, 24, 4219, 4222, Jun. 2007
English, Scientific journal

Chiroptical analysis of glycoconjugates by vibrational circular dichroism (VCD)
Taniguchi Tohru, Monde Kenji
TRENDS IN GLYCOSCIENCE AND GLYCOTECHNOLOGY, 19, 107, 147, 164, May 2007, [Peer-reviewed]
English, Scientific journal

Vibrational circular dichroism (VCD) studies on disaccharides in the CH region: toward discrimination of the glycosidic linkage position
Tohru Taniguchi, Kenji Monde
ORGANIC & BIOMOLECULAR CHEMISTRY, 5, 7, 1104, 1110, 2007
English, Scientific journal

Absolute configuration determination using vibrational circular dichroism. Method for absolute configuration determination in the solution state without induction.
Kenji Monde, Nobuaki Miura, Tohru Taniguchi
Kagaku to Seibutsu, 45, 7, 455, 458, 日本農芸化学会, 2007
Japanese

Rewinding of Helical Systems by Use of the Cr(III) Complex as a Photoresponsive Chiral Dopant
Tohru Taniguchi, Kenji Monde, Shin-Ichiro Nishimura, Jun Yoshida, Hisako Sato, Akihiko Yamagishi
Molecular Crystals and Liquid Crystals, 460, 1, 107, 116, Informa UK Limited, 01 Dec. 2006
Scientific journal

Vibrational Circular Dichroism : New Chiroptical Spectroscopy without UV-VIS Chromophores
MONDE Kenji
Kobunshi, 55, 7, 516, 519, The Society of Polymer Science, Japan, 01 Jul. 2006
Japanese

Absolute configurations of endoperoxides determined by vibrational circular dichroism (VCD)
Kenji Monde, Tohru Taniguchi, Nobuaki Miura, Charles S. Vairappan, Minoru Suzuki
TETRAHEDRON LETTERS, 47, 26, 4389, 4392, Jun. 2006
English, Scientific journal

Absolute configurations of brominated sesquiterpenes determined by vibrational circular dichroism
K Monde, T Taniguchi, N Miura, CS Vairappan, M Suzuki
CHIRALITY, 18, 5, 335, 339, May 2006
English, Scientific journal

Conformational analysis of chiral helical perfluoroalkyl chains by VCD
Kenji Monde, Nobuaki Miura, Mai Hashimoto, Tohru Taniguchi, Tamotsu Inabe
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 128, 18, 6000, 6001, May 2006
English, Scientific journal

Dramatic effects of d-electron configurations on vibrational circular dichroism spectra of tris(acetylacetonato)metal(III)
Hisako Sato, Tohru Taniguchi, Kenji Monde, Shin-Ichiro Nishimura, Akihiko Yamagishi
CHEMISTRY LETTERS, 35, 4, 364, 365, Apr. 2006
English, Scientific journal

A theoretical study of alpha- and beta-D-glucopyranose conformations by the density functional theory
N Miura, T Taniguchi, K Monde, SI Nishimura
CHEMICAL PHYSICS LETTERS, 419, 4-6, 326, 332, Feb. 2006
English, Scientific journal

High throughput quantitative glycomics and glycoform-focused proteomics of murine dermis and epidermis
R Uematsu, J Furukawa, H Nakagawa, Y Shinohara, K Deguchi, K Monde, SI Nishimura
MOLECULAR & CELLULAR PROTEOMICS, 4, 12, 1977, 1989, Dec. 2005
English, Scientific journal

Rational design, synthesis, and characterization of novel inhibitors for human beta 1,4-galactosyltransferase
K Takaya, N Nagahori, M Kurogochi, T Furuike, N Miura, K Monde, YC Lee, SI Nishimura
JOURNAL OF MEDICINAL CHEMISTRY, 48, 19, 6054, 6065, Sep. 2005
English, Scientific journal

Chiral cruciferous phytoalexins: Preparation, absolute configuration, and biological activity
K Monde, T Taniguchi, N Miura, P Kutschy, Z Curillova, M Pilatova, J Mojzis
BIOORGANIC & MEDICINAL CHEMISTRY, 13, 17, 5206, 5212, Sep. 2005, [Peer-reviewed]
English, Scientific journal

Versatile glycoblotting nanoparticles for high-throughput protein glycomics
K Niikura, R Kamitani, M Kurogochi, R Uematsu, Y Shinohara, H Nakagawa, K Deguchi, K Monde, H Kondo, SI Nishimura
CHEMISTRY-A EUROPEAN JOURNAL, 11, 13, 3825, 3834, Jun. 2005
English, Scientific journal

Cruciferous phytoalexins: antiproliferative effects in T-Jurkat leukemic cells
M Pilatova, M Sarissky, P Kutschy, A Mirossay, R Mezencev, Z Curillova, M Suchy, K Monde, L Mirossay, J Mojzis
LEUKEMIA RESEARCH, 29, 4, 415, 421, Apr. 2005
English, Scientific journal

Antihyperglycaemic flavonoids from Syzygium samarangense (Blume) Merr. and Perry
MHC Resurreccion-Magno, IM Villasenor, N Harada, K Monde
PHYTOTHERAPY RESEARCH, 19, 3, 246, 251, Mar. 2005
English, Scientific journal

Feasibility of chitosan-based hyaluronic acid hybrid biomaterial for a novel scaffold in cartilage tissue engineering
S Yamane, N Iwasaki, T Majima, T Funakoshi, T Masuko, K Harada, A Minami, K Monde, S Nishimura
BIOMATERIALS, 26, 6, 611, 619, Feb. 2005
English, Scientific journal

Chemical and enzymatic synthesis of glycocluster having seven sialyl lewis X arrays using beta-cyclodextrin as a key scaffold material
T Furuike, R Sadamoto, K Niikura, K Monde, N Sakairi, SI Nishimura
TETRAHEDRON, 61, 7, 1737, 1742, Feb. 2005
English, Scientific journal

High-throughput protein glycomics: Combined use of chemoselective glycoblotting and MALDI-TOF/TOF mass spectrometry
SI Nishimura, K Niikura, M Kurogochi, T Matsushita, M Fumoto, H Hinou, R Kamitani, H Nakagawa, K Deguchi, N Miura, K Monde, H Kondo
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 44, 1, 91, 96, 2005
English, Scientific journal

Direct observation of sugar-protein, sugar-sugar, and sugar-water complexes by cold-spray ionization time-of-flight mass spectrometry
SI Nishimura, N Nagahori, K Takaya, Y Tachibana, N Miura, K Monde
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 44, 4, 571, 575, 2005
English, Scientific journal

Versatile synthesis of oligosaccharide-containing fullerenes
S Abe, H Moriyama, K Niikura, F Fei, K Monde, S Nishimura
TETRAHEDRON-ASYMMETRY, 16, 1, 15, 19, Jan. 2005
English, Scientific journal

Assignment and quantification of 2-aminopyridine derivatized oligosaccharide isomers coeluted on reversed-phase HPLC/MS by MSn spectral library
Y Takegawa, K Deguchi, S Ito, S Yoshioka, A Sano, K Yoshinari, K Kobayashi, H Nakagawa, K Monde, SI Nishimura
ANALYTICAL CHEMISTRY, 76, 24, 7294, 7303, Dec. 2004
English, Scientific journal

Glycoinsulins: Dendritic sialyloligosaccharide-displaying insulins showing a prolonged blood-sugar-lowering activity
Masaaki Sato, Tetsuya Furuike, Reiko Sadamoto, Naoki Fujitani, Taku Nakahara, Kenichi Niikura, Kenji Monde, Hirosato Kondo, Shin-Ichiro Nishimura
Journal of the American Chemical Society, 126, 43, 14013, 14022, 03 Nov. 2004
English, Scientific journal

A characteristic CH band in VCD of methyl glycosidic carbohydrates
T Taniguchi, K Monde, N Miura, S Nishimura
TETRAHEDRON LETTERS, 45, 46, 8451, 8453, Nov. 2004
English, Scientific journal

Glycoinsulins: Dendritic sialyloligosaccharide-displaying insulins showing a prolonged blood-sugar-lowering activity
M Sato, T Furuike, R Sadamoto, N Fujitani, T Nakahara, K Niikura, K Monde, H Kondo, SI Nishimura
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 126, 43, 14013, 14022, Nov. 2004, [Peer-reviewed]
English, Scientific journal

Sequential glycoproteins: Practical method for the synthesis of antifreeze glycoprotein models containing base labile groups
Y Tachibana, K Monde, SI Nishimura
MACROMOLECULES, 37, 18, 6771, 6779, Sep. 2004
English, Scientific journal

Specific band observed in VCD predicts the anomeric configuration of carbohydrates
K Monde, T Taniguchi, N Miura, SI Nishimura
J. Am. Chem. Soc., 126, 31, 9496, 9497, Aug. 2004, [Peer-reviewed]
English, Scientific journal

Synthesis of 4-fluorinated UDP-MurNAc pentapeptide as an inhibitor of bacterial growth
T Ueda, F Feng, R Sadamoto, K Niikura, K Monde, SI Nishimura
ORGANIC LETTERS, 6, 11, 1753, 1756, May 2004
English, Scientific journal

Feasibility of polysaccharide hybrid materials for scaffolds in cartilage tissue engineering: Evaluation of chondrocyte adhesion to polyion complex fibers prepared from alginate and chitosan
N Iwasaki, ST Yamane, T Majima, Y Kasahara, A Minami, K Harada, S Nonaka, N Maekawa, H Tamura, S Tokura, M Shiono, K Monde, SI Nishimura
BIOMACROMOLECULES, 5, 3, 828, 833, May 2004
English, Scientific journal

Control of bacteria adhesion by cell-wall engineering
R Sadamoto, K Niikura, T Ueda, K Monde, N Fukuhara, SI Nishimura
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 126, 12, 3755, 3761, Mar. 2004
English, Scientific journal

An engineered hyaluronan synthase - Characterization of recombinant human hyaluronan synthase 2 expressed in Escherichia coli
H Hoshi, H Nakagawa, S Nishiguchi, K Iwata, K Niikura, K Monde, SI Nishimura
JOURNAL OF BIOLOGICAL CHEMISTRY, 279, 4, 2341, 2349, Jan. 2004
English, Scientific journal

Antifreeze glycoproteins: Elucidation of the structural motifs that are essential for antifreeze activity
Y Tachibana, GL Fletcher, N Fujitani, S Tsuda, K Monde, SI Nishimura
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 43, 7, 856, 862, 2004
English, Scientific journal

Site-specific introduction of sialic acid into insulin
M Sato, R Sadamoto, K Niikura, K Monde, H Kondo, SI Nishimura
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 43, 12, 1516, 1520, 2004
English, Scientific journal

Structural assignment of isomeric 2-aminopyridine-derivatized oligosaccharides using MSn spectral matching
Y Takegawa, S Ito, S Yoshioka, K Deguchi, H Nakagawa, K Monde, SI Nishimura
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 18, 4, 385, 391, 2004
English, Scientific journal

Fluorescent glyconanoparticles as a sensitive device to monitor sugar-involving molecular events
K Niikura, N Osuga, N Nagahori, R Sadamoto, M Shiono, N Iwasaki, K Monde, A Minami, SI Nishimura
POLYMER JOURNAL, 36, 3, 209, 218, 2004
English, Scientific journal

Chemo-enzymatic synthesis of fluorinated 2-N-acetamidosugar nucleotides using UDP-GlcNAc pyrophosphorylase
F Feng, K Okuyama, K Niikura, T Ohta, R Sadamoto, K Monde, T Noguchi, SI Nishimura
ORGANIC & BIOMOLECULAR CHEMISTRY, 2, 11, 1617, 1623, 2004
English, Scientific journal

Artificial golgi apparatus: Direct monitoring of glycosylation reactions on automated glycosynthesizer
SI Nishimura, N Nagahori, R Sadamoto, K Monde, K Niikura
SYNTHESIS OF CARBOHYDRATES THROUGH BIOTECHNOLOGY, 873, 113, 124, 2004, [Peer-reviewed]
English, Scientific journal

Preparation of cruciferous phytoalexin related metabolites, (-)-dioxibrassinin and (-)-3-cyanomethyl-3-hydroxyoxindole, and determination of their absolute configurations by vibrational circular dichroism (VCD)
K Monde, T Taniguchi, N Miura, SI Nishimura, N Harada, RK Dukor, LA Nafie
TETRAHEDRON LETTERS, 44, 32, 6017, 6020, Aug. 2003
English, Scientific journal

Glycosyltransferase microarray displayed on the glycolipid LB membrane
N Nagahori, K Niikura, R Sadamoto, M Taniguchi, A Yamagishi, K Monde, SI Nishimura
ADVANCED SYNTHESIS & CATALYSIS, 345, 6-7, 729, 734, Jun. 2003
English, Scientific journal

An efficient synthesis of a biantennary sialooligosaccharide analog using a 1,6-anhydro-beta-lactose derivative as a key synthetic block
T Furuike, K Yamada, T Ohta, K Monde, SI Nishimura
TETRAHEDRON, 59, 27, 5105, 5113, Jun. 2003
English, Scientific journal

Synthesis of photopolymerizable glycolipids and their application as scaffolds to immobilize proteins with a micron-sized pattern
N Nagahori, K Niikura, R Sadamoto, K Monde, SI Nishimura
AUSTRALIAN JOURNAL OF CHEMISTRY, 56, 6, 567, 576, 2003
English, Scientific journal

Glycotentacles: Synthesis of cyclic glycopeptides, toward a tailored blocker of influenza virus hemagglutinin
T Ohta, N Miura, N Fujitani, F Nakajima, K Niikura, R Sadamoto, CT Guo, T Suzuki, Y Suzuki, K Monde, SI Nishimura
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 42, 42, 5186, 5189, 2003
English, Scientific journal

Cell wall engineering of living bacteria through biosynthesis.
Sadamoto R, Niikura K, Monde K, Nishimura S
Methods in enzymology, 362, 273, 286, 2003, [Peer-reviewed]

Efficient and versatile synthesis of mucin-like glycoprotein mimics
Y Tachibana, N Matsubara, F Nakajima, T Tsuda, S Tsuda, K Monde, SI Nishimura
TETRAHEDRON, 58, 51, 10213, 10224, Dec. 2002
English, Scientific journal

Spirocyclization strategy toward indole phytoalexins. The first synthesis of (+/-)-1-methoxyspirobrassinin, (+/-)-1-methoxyspirobrassinol, and (+/-)-1-methoxyspirobrassinol methyl ether
P Kutschy, M Suchy, K Monde, N Harada, R Maruskova, Z Curillova, M Dzurilla, M Miklosova, R Mezencev, J Mojzis
TETRAHEDRON LETTERS, 43, 52, 9489, 9492, Dec. 2002
English, Scientific journal

Cell-wall engineering of living bacteria
R Sadamoto, K Niikura, PS Sears, HT Liu, CH Wong, A Suksomcheep, F Tomita, K Monde, SI Nishimura
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 124, 31, 9018, 9019, Aug. 2002
English, Scientific journal

Absolute stereochemistry of chiral C-60 fullerene bis-adducts
K Yoshida, S Osawa, K Monde, M Watanabe, N Harada
ENANTIOMER, 7, 1, 23, 32, Jan. 2002
English, Scientific journal

Erythrocyte-like liposomes prepared by means of amphiphilic cyclodextrin sulfates
T Sukegawa, T Furuike, K Niikura, A Yamagishi, K Monde, SI Nishimura
CHEMICAL COMMUNICATIONS, 430, 5, 430, 431, 2002
English, Scientific journal

Measurement of interfluorine distances in solids
ML Gilchrist, K Monde, Y Tomita, T Iwashita, K Nakanishi, AE McDermott
JOURNAL OF MAGNETIC RESONANCE, 152, 1, 1, 6, Sep. 2001
English, Scientific journal

Synthesis, absolute configuration, and enantiomeric enrichment of a cruciferous oxindole phytoalexin, (S)-(-)-spirobrassinin, and its oxazoline analog
M Suchy, P Kutschy, K Monde, H Goto, N Harada, M Takasugi, M Dzurilla, E Balentova
JOURNAL OF ORGANIC CHEMISTRY, 66, 11, 3940, 3947, Jun. 2001
English, Scientific journal

Enantiomeric excess of a cruciferous phytoalexin, spirobrassinin, and its enantiomeric enrichment in an achiral HPLC system
K Monde, N Harada, M Takasugi, P Kutschy, M Suchy, M Dzurilla
JOURNAL OF NATURAL PRODUCTS, 63, 9, 1312, 1314, Sep. 2000
English, Scientific journal

Synthesis and absolute stereochemistry of a cruciferous phytoalexin, (-)-spirobrassinin
K Monde, S Osawa, N Harada, M Takasugi, M Suchy, P Kutschy, M Dzurilla, E Balentova
CHEMISTRY LETTERS, 29, 8, 886, 887, Aug. 2000
English, Scientific journal

Design and preparation of polyphenyl distance markers for solid-state F-19 NMR
K Monde, Y Tomita, ML Gilchrist, AE McDermott, K Nakanishi
ISRAEL JOURNAL OF CHEMISTRY, 40, 3-4, 301, 306, 2000
English, Scientific journal

Phytoalexins from Brassica (Cruciferae) as oviposition stimulants for the cabbage root fly, Delia radicum
Robert Baur, Erich Staedler, Kenji Monde, Mitsuo Takasugi
CHEMOECOLOGY, 8, 4, 163, 168, Dec. 1998
English, Scientific journal

Organochlorine compounds from a terrestrial higher plant: Structures and origin of chlorinated orcinol derivatives from diseased bulbs of Lilium maximowiczii
K Monde, H Satoh, M Nakamura, M Tamura, M Takasugi
JOURNAL OF NATURAL PRODUCTS, 61, 7, 913, 921, Jul. 1998
English, Scientific journal

Synthesis and optical resolution of a fluorescent chiral calix[4]arene with two pyrene moieties forming an intramolecular excimer
T Jin, K Monde
CHEMICAL COMMUNICATIONS, 1998, 13, 1357, 1358, Jul. 1998
English, Scientific journal

Trapping experiment with aniline for a biosynthetic intermediate of sulfur-containing cruciferous phytoalexins
K Monde, A Tanaka, M Takasugi
JOURNAL OF ORGANIC CHEMISTRY, 61, 25, 9053, 9054, Dec. 1996
English, Scientific journal

Identification of an ornithine-containing lipid from Cytophaga johnsonae Stanier strain C21 by H-1-NMR
H Okuyama, K Monde
CHEMISTRY AND PHYSICS OF LIPIDS, 83, 2, 169, 173, Sep. 1996
English, Scientific journal

Isolation and Biological Activity of Toxins Produced by a Japanese Strain of Pseudomonas tolaasii, the Pathogen of Bacterial Rot of Cultivated Oyster Mushroom.
Akira SHIRATA, Kazuhisa SUGAYA, Mitsuo TAKASUGI, Kenji MONDE
Japanese Journal of Phytopathology, 61, 5, 493, 502, The Phytopathological Society of Japan, Oct. 1995
Scientific journal

STUDIES ON STRESS METABOLITES .20. 3 SULFUR-CONTAINING STRESS METABOLITES FROM JAPANESE RADISH
K MONDE, M TAKASUGI, A SHIRATA
PHYTOCHEMISTRY, 39, 3, 581, 586, Jun. 1995
English, Scientific journal

No involvement of methoxybrassinin in the biosynthesis of cyclobrassinin
Kenji Monde, Kimio Tamura, Mitsuo Takasugi
Phytochemistry, 39, 3, 587, 589, 1995
English, Scientific journal

A NEW APPROACH IN EXCITON-COUPLED CIRCULAR-DICHROISM (ECCD) - INSERTION OF AN AUXILIARY STEREOGENIC CENTER
RV PERSON, K MONDE, HU HUMPF, N BEROVA, K NAKANISHI
CHIRALITY, 7, 3, 128, 135, 1995
English, Scientific journal

Cruciferous Phytoalexins
Kenji Monde, Mitsuo Takasugi
Journal of Pesticide Science, 20, 3, 339, 343, 1995, [Peer-reviewed]
English, Scientific journal

STUDIES ON STRESS METABOLITES .19. BIOSYNTHESIS OF CRUCIFEROUS PHYTOALEXINS
K MONDE, M TAKASUGI, T OHNISHI
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 116, 15, 6650, 6657, Jul. 1994
English, Scientific journal

Dehydro-4-methoxycyclobrassinin, a Sulfur-containing Phytoalexin Isolated from Turnip Brassica campestris L. ssp. rapa
Mitsuo Takasugi, Kenji Monde, Kimio Tamura, Kensuke Kobayashi, Masanori Somei
HETEROCYCLES, 38, 2, 263, 263, The Japan Institute of Heterocyclic Chemistry, 1994
Scientific journal

STUDIES ON STRESS METABOLITES .17. YURINELIDE, A NOVEL 3-BENZYLIDENE-1,4-BENZODIOXIN-2(3H)-ONE PHYTOALEXIN FROM LILIUM-MAXIMOWICZII
K MONDE, M KISHIMOTO, M TAKASUGI
TETRAHEDRON LETTERS, 33, 37, 5395, 5398, Sep. 1992
English, Scientific journal

Lipoamino acids and sulfonoplipids in Cytophaga johnsonae Stanier strain C21 and six related species of Cytophaga
Ryoh Kawazoe, Kenji Monde, Wolfgang Reichardt, Hidetoshi Okuyama
Archives of Microbiology, 158, 3, 171, 175, Springer-Verlag, Aug. 1992, [Peer-reviewed]
English, Scientific journal

STUDIES ON STRESS METABOLITES .16. HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC ANALYSIS OF CRUCIFEROUS PHYTOALEXINS USING COMPLEX TERNARY MOBILE PHASE GRADIENTS
K MONDE, M TAKASUGI
JOURNAL OF CHROMATOGRAPHY, 598, 1, 147, 152, May 1992
English

STUDIES ON STRESS METABOLITES .14. BIOSYNTHESIS OF CRUCIFEROUS PHYTOALEXINS - THE INVOLVEMENT OF A MOLECULAR REARRANGEMENT IN THE BIOSYNTHESIS OF BRASSININ
K MONDE, M TAKASUGI
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, 22, 1582, 1583, Nov. 1991
English, Scientific journal

TIME-COURSE STUDIES OF PHYTOALEXINS AND GLUCOSINOLATES IN UV-IRRADIATED TURNIP TISSUE
K MONDE, M TAKASUGI, JA LEWIS, GR FENWICK
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES, 46, 3-4, 189, 193, Mar. 1991
English, Scientific journal

BRASSICANAL C AND 2-DIOXINDOLES FROM CABBAGE
K MONDE, K SASAKI, A SHIRATA, M TAKASUGI
PHYTOCHEMISTRY, 30, 9, 2915, 2917, 1991
English, Scientific journal

STUDIES ON STRESS METABOLITES .15. METHOXYBRASSENIN-A AND METHOXYBRASSENIN-B, SULFUR-CONTAINING STRESS METABOLITES FROM BRASSICA-OLERACEA VAR CAPITATA
K MONDE, K SASAKI, A SHIRATA, M TAKASUGI
PHYTOCHEMISTRY, 30, 12, 3921, 3922, 1991
English, Scientific journal

STUDIES ON STRESS METABOLITES .11. TOTAL SYNTHESIS OF LETTUCENIN-A, A GUAIANOLIDE PHYTOALEXIN FROM LACTUCA-SATIVA VAR CAPITATA
K MONDE, M TAKASUGI, N KATSUI, T MASAMUNE
CHEMISTRY LETTERS, 19, 8, 1283, 1286, Aug. 1990
English, Scientific journal

STUDIES ON STRESS METABOLITES .8. BRASSICANAL-A AND BRASSICANAL-B, NOVEL SULFUR-CONTAINING PHYTOALEXINS FROM THE CHINESE CABBAGE BRASSICA-CAMPESTRIS L SSP PEKINENSIS
K MONDE, N KATSUI, A SHIRATA, M TAKASUGI
CHEMISTRY LETTERS, 19, 2, 209, 210, Feb. 1990
English, Scientific journal

A guaianolide phytoalexin, cichoralexin, from Cichorium intybus
Kenji Monde, Toyohisa Oya, Akira Shirata, Mitsuo Takasugi
Phytochemistry, 29, 11, 3449, 3451, 1990
English, Scientific journal

STUDIES ON STRESS METABOLITES .9. 4-METHOXYBRASSININ, A SULFUR-CONTAINING PHYTOALEXIN FROM BRASSICA-OLERACEA
K MONDE, K SASAKI, A SHIRATA, M TAKASUGI
PHYTOCHEMISTRY, 29, 5, 1499, 1500, 1990
English, Scientific journal

STUDIES ON STRESS METABOLITES .7. NOVEL SULFUR-CONTAINING PHYTOALEXINS FROM THE CHINESE CABBAGE BRASSICA-CAMPESTRIS L SSP PEKINENSIS (CRUCIFERAE)
M TAKASUGI, K MONDE, N KATSUI, A SHIRATA
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 61, 1, 285, 289, Jan. 1988
English, Scientific journal

ANTIFUNGAL COMPOUNDS FROM DIOSCOREA-BATATAS INOCULATED WITH PSEUDOMONAS-CICHORII
M TAKASUGI, S KAWASHIMA, K MONDE, N KATSUI, T MASAMUNE, A SHIRATA
PHYTOCHEMISTRY, 26, 2, 371, 375, 1987
English, Scientific journal

STUDIES ON STRESS METABOLITES .6. SPIROBRASSININ, A NOVEL SULFUR-CONTAINING PHYTOALEXIN FROM THE DAIKON RHAPHANUS-SATIVUS L VAR HORTENSIS (CRUCIFERAE)
M TAKASUGI, K MONDE, N KATSUI, A SHIRATA
CHEMISTRY LETTERS, 16, 8, 1631, 1632, 1987
English, Scientific journal

-
門出 健次, 有機合成化学協会誌, 82, 2, 115, 115, Feb. 2024
The Society of Synthetic Organic Chemistry, Japan, Japanese, Introduction scientific journal

ケモエンザイマティカルな長鎖塩基の調製と樹脂固定型グルタルアルデヒドによる効率的精製法
門出 健次, 村井 勇太, 生化学, 92, 2, 272, 277, Apr. 2020, [Domestic magazines]
Japanese

Vibrational CD spectroscopy as a powerful tool for chiral analysis of flavor compounds
Kenji Monde, Atsufumi Nakahashi, Nobuaki Miura, Tohru Taniguchi, Yoshihiro Yaguchi, Daisuke Sugimoto, Makoto Emura, ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 248, Aug. 2014
English, Summary international conference

Exciton Chirality Method in Vibrational Circular Dichroism
MONDE Kenji, 高分子, 61, 10, 779, 780, 01 Oct. 2012
Japanese

キラル多核金属錯体の振動円二色性スペクトルによる研究
SATO HISAKO, TANIGUCHI TOORU, MONDE KENJI, FUKUDA YUTAKA, YAMAGISHI AKIHIKO, 錯体化学討論会講演要旨集, 57th, 192, 10 Sep. 2007
Japanese

A challenge to describe the functional networks of glycoconjugates: "Glyconet" in a database "Glycoconjugate Data Bank"
Nobuaki Miura, Kazuko Hirose, Tomonori Ito, Ryo Hashimoto, Nobuhiro Fukushima, Kenji Monde, Shin-Ichiro Nishimura, GLYCOBIOLOGY, 16, 11, 1123, 1124, Nov. 2006
English, Summary international conference

A glycomic approach to drug resistance: Direct interaction between Cisplatin and N-glycans
Hiroaki Nakagawa, Shinji Hayashi, Shigeaki Abe, Noriko Nagahori, Kenji Monde, Miki Ichikawa-Ohira, Hirosato Kondo, Shin-Ichi Akiyama, Kisaburo Deguchi, Akira Nakagawara, Shin-Ichiro Nishimura, GLYCOBIOLOGY, 16, 11, 1150, 1150, Nov. 2006
English, Summary international conference

Novel chiroptical analysis of glycoconjugates by Vibrational Circular Dichroism (VCD)
Kenji Monde, Tohru Taniguchi, Masami Fukuzawa, Mai Hashimoto, Atsufumi Nakahashi, Nobuaki Miura, Shin-Ichiro Nishimura, GLYCOBIOLOGY, 16, 11, 1136, 1137, Nov. 2006
English, Summary international conference

トリスキレート型金属錯体の光学分割とVCD
SATO HISAKO, TANIGUCHI TOORU, MONDE KENJI, NISHIMURA SHIN'ICHIRO, YAMAGISHI AKIHIKO, 錯体化学討論会講演要旨集, 56th, 326, 08 Sep. 2006
Japanese

トリスおよびビスアセチルアセトナト金属錯体のVCD測定と理論計算
SATO HISAKO, TANIGUCHI TOORU, MONDE KENJI, NISHIMURA SHIN'ICHIRO, YAMAGISHI AKIHIKO, 錯体化学討論会講演要旨集, 56th, 34, 08 Sep. 2006
Japanese

Modification of Chitosan with Bioactive Oligosaccharide
LI Xuebing, WATANABE Shinya, SUZUKI Takashi, SUZUKI Yasuo, WATANABE Miho, NATORI Yasuhiro, NISHIKAWA Kiyotaka, KITA Eiji, MONDE Kenji, NISHIMURA Shin-Ichiro, キチン・キトサン研究 = Chitin and chitosan research, 11, 2, 120, 121, 01 Jul. 2005
Japanese

Specific band observed in VCD predicts the anorneric configuration of carbohydrates (vol 126, pg 9496, 2004)
K Monde, T Taniguchi, N Miura, SI Nishimura, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 127, 16, 6133, 6133, Apr. 2005
English, Others

Structural assignment of isomeric 2-aminopyridine-derivatized oligosaccharides using MSn spectral matching (vol 18, pg 385, 2004)
Y Takegawa, S Ito, S Yoshioka, K Deguchi, H Nakagawa, K Monde, SI Nishimura, RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 19, 4, 588, 588, 2005
English, Others

Vibrational circular dichroism: Chiroptical analysis of biomolecules
T Taniguchi, N Miura, SI Nishimura, K Monde, MOLECULAR NUTRITION & FOOD RESEARCH, 48, 4, 246, 254, Sep. 2004
English

Synthesis of 4-fluorinated UDP-MurNAc pentapeptide as an inhibitor of bacterial growth (vol 6, pg 1753, 2004)
T Ueda, F Feng, R Sadamoto, K Niikura, K Monde, SI Nishimura, ORGANIC LETTERS, 6, 14, 2489, 2489, Jul. 2004
English, Others

Functional glycoclusters having chitosan skeleton
LI Xuebing, WATANABE Shinya, SUZUKI Takashi, SUZUKI Yasuo, NATORI Yasuhiro, NISHIKAWA Kiyotaka, MONDE Kenji, NISHIMURA Shin-Ichiro, キチン・キトサン研究 = Chitin and chitosan research, 10, 2, 204, 205, 01 Jul. 2004
Japanese

糖鎖付加インスリンのデザインと機能
佐藤公昭, 貞許礼子, 藤谷直樹, 中原拓, FENG F, 新倉謙一, 門出健次, 西村紳一郎, 近藤裕郷, 高分子学会予稿集(CD-ROM), 53, 1, IH14, 10 May 2004
Japanese

71(P-61) Stereochemical Studies of Glycoconjugates by Vibrational Circular Dichroism (VCD)
Taniguchi Tohru, Miura Nobuaki, Uchida Naoto, Nishimura Shin-Ichiro, Monde Kenji, Symposium on the Chemistry of Natural Products, symposium papers, 46, 0, 401, 406, 2004
Chiral molecules exhibit circular dichroism (CD), the differential absorption of left versus right circularly polarized light, and the spectroscopies have been useful method for determining the absolute configuration. Recently, the measurement of CD in an infrared region, i.e. vibrational circular dichroism (VCD), has been advanced instrumentally and theoretically. VCD has some advantages over conventional electronic circular dichroism (ECD) by the applicability to all organic molecules and the reliability of ab initio quantum calculations. We apply this powerful technique to the determination of the absolute stereochemistry of some cruciferous phytoalexin-related compounds and to analysis of glycoconjugates. The determination of the absolute configuration of cruciferous phytoalexin-related compounds A number of cruciferous phytoalexin studies have been reported so far, but most of their absolute stereochemistry is still to be investigated. So we applied the VCD spectroscopy to determine the absolute configuration of dioxibrassinin (1) and 3-cyanomethyl-3-hydroxyoxindole (2). Compounds 1 and 2 were synthesized and their VCD spectra were measured. The comparison of observed VCD spectra and calculated ones indicated that their stereochemistry are both S. This is the first case of the determination of absolute stereochemistry of chiral tertiary alcohols by VCD. Application of VCD to carbohydrates Recently, the biological significance of carbohydrates have been recognized and analytical studies of carbohydrates have been widely investigated. Most analyses have been based on achiral methods such as NMR or MS in spite of their chiral properties. We considered that the detailed stereochemical information could be extracted using VCD. Various carbohydrates have been measured to construct an extensive database aiming to create a methodology for VCD pattern discrimination of the carbohydrates. The database in the fingerprint region indicated that sugars with the axial glycosidic linkage showed a negative, sharp and intense VCD band, named "Glycoside band" at around 1145 cm^<-1>. The applicability of the Glycoside band was demonstrated by quantifying α-β ratio of mixture samples and monitoring of an enzymatic reaction. In the C-H stretching region, we found the stereochemistry of single chiral center in the presence of multiple such centers could be extracted through the vibrational chirality transfer phenomenon. Also, VCD in this region was indicated to be a sensitive probe of glycosidic linkage sites. In conclusion, by using the VCD database and the proposed spectra-structure correlations, VCD will be an effective tool in carbohydrate analysis., Symposium on the Chemistry of Natural Products Steering Committee, Japanese

Conformational anlyses of carbohydrates by the molecular orbital theory and VCD spectra
Miura Nobuaki, Taniguchi Tohru, Monde Kenji, Nishimura Shin-Ichiro, Abstracts of Symposium on Physical Organic Chemistry, 17, 0, 51, 51, 2004
糖鎖は不斉炭素の集合体であり、その配座解析の確固たる方法論が未だにない。我々は配座解析の強力なツールとして分子軌道法を用い、不斉性を検出可能な振動領域円二色性スペクトルを計算することによって、測定されたスペクトルを再現することによって糖鎖の配座を混合比のレベルでの解析を行う。, The Society of Physical Organic Chemistry, Japan

N-glycan patterns of human serum in rheumatoid arthritis
M Hato, H Nakagawa, Y Takegawa, K Deguchi, K Monde, N Iwasaki, A Minami, H Kondo, SI Nishimura, GLYCOBIOLOGY, 13, 11, 870, 870, Nov. 2003
English, Summary international conference

Structural assignment of isomeric 2-aminopyridine derivatized oligosaccharides using Ms-n spectral matching
Y Takegawa, S Ito, S Yoshioka, K Deguchi, H Nakagawa, K Monde, SI Nishimura, GLYCOBIOLOGY, 13, 11, 844, 845, Nov. 2003
English, Summary international conference

Structures of N-glycan from human dermis
R Uematsu, H Nakagawa, K Deguchi, M Ota, K Yokota, H Shimizu, K Monde, SI Nishimura, GLYCOBIOLOGY, 13, 11, 846, 846, Nov. 2003
English, Summary international conference

Glycoblotting: Synthetic nanoparticles for rapid isolation and analysis of glycopatterns
SI Nishimura, K Niikura, N Nagahori, R Uematsu, H Nakagawa, S Abe, H Moriyama, R Sadamoto, K Deguchi, K Monde, H Kondo, GLYCOBIOLOGY, 13, 11, 843, 844, Nov. 2003
English, Summary international conference

不凍糖タンパク質モデル分子の設計と機能発現メカニズムの解明
立花裕樹, 五十嵐幸太, 藤谷直樹, 津田栄, 門出健次, 西村紳一郎, 高分子学会予稿集, 52, 13, 3755, 3756, 10 Sep. 2003
Japanese

抗インフルエンザウイルス活性を有する環状糖ペプチドの設計と評価
太田尚志, 藤谷直樹, 三浦信明, 新倉謙一, 鈴木隆, 鈴木康夫, 門出健次, 西村紳一郎, 高分子学会予稿集, 52, 13, 3789, 3790, 10 Sep. 2003
Japanese

Synthesis and characterization of functional glycolipid LB membrane.
N Nagahori, R Sadamoto, K Niikura, K Monde, SI Nishimura, ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 226, U200, U200, Sep. 2003
English, Summary international conference

Stereochemical chiral analysis of carbohydrates by vibrational circular dichroism.
K Monde, T Taniguchi, N Miura, SI Nishimura, ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 226, U213, U213, Sep. 2003
English, Summary international conference

抗インフルエンザウイルス活性を有する環状糖ペプチドの設計と評価
太田尚志, 藤谷直樹, 三浦信明, 新倉謙一, 鈴木隆, 鈴木康夫, 門出健次, 西村紳一郎, 日本化学会北海道支部研究発表会講演要旨集, 2003, 56, 01 Jul. 2003
Japanese

21 Synthetic studies on glycopeptide polymers having ice crystal growth inhibition activity
Tachibana Yuki, Igarashi Kota, Monde Kenji, Nishimura Shin-Ichiro, Tsuda Sakae, Symposium on the Chemistry of Natural Products, symposium papers, 44, 0, 121, 126, 2002
Antifreeze glycoproteins [AFGPs: {Ala-Thr(Galβ1-3GalNAcα)-Ala}_n, n=4-50] in the serum of polar fishes have been known to depress the freezing point of their blood and help them to survive at the temperature below-1.9℃[1]. Though it is widely accepted that AFGPs bind to the ice surface and prevent its growth, the definitive molecular mechanism of the action has not been solved yet. In this study, structure-activity relationships in AFGPs were studied toward understanding of the mechanism, thorough chemical syntheses, activity evaluations, and conformational analyses of the AFGP and its analogues, in which sugar or peptide moieties were different from those of the wild-type AFGP. The AFGP (1) and its analogues (2-8) were successfully synthesized via simple polymerization of their repeating unit using a DPPA method without any protection of sugar -OH groups [2]. Additionally, sialyl T-bearing glycopolypeptide (9) was successfully prepared through enzymatic elongation of a sialic acid residue to C-3 position of the galactose residue in the AFGP (1), indicating the broad applicability of this methodology for the syntheses of various glycopeptide polymers. In the evaluation assay of the antifreeze activity, artificial AFGP (1) showed similar activity as that of the wild-type AFGP. On the contrary, neither an AFGP repeating unit glycopeptide (19) nor a sugar-lacked polypeptide (poly-ATA, 8) shows the activity. Interestingly, AFGP analogs having GalNAc (2) or LacNAc (3) as sugar moiety showed similar activities as AFGP, while that of Galactose (4), Lactose (5), β-O-linked (6), and ASA (7) did not. These results clearly indicate the importance of i) repeating structure of glycopeptide, ii) NHAc group at C-2 position of the sugar moiety directly attached to the peptide, iii) α-glycosidic linkage between the sugar and the threonyl residue, for the specific interaction with ice. Furthermore, secondary structural analyses of the synthetic compounds were carried out by means of a CD spectroscopic method, in order to clarify the relationships between their conformations and their activities. The CD spectra of active compounds (1-3) were obviously different from those of inactive analogues (4-8), suggesting the presence of an ordered structure, but not α-helix., Symposium on the Chemistry of Natural Products Steering Committee, Japanese

CRUCIFEROUS PHYTOALEXINS
K MONDE, M TAKASUGI, JOURNAL OF PESTICIDE SCIENCE, 20, 3, 339, 343, 1995
Japanese, Introduction scientific journal

STUDIES ON STRESS METABOLITES .18. DEHYDRO-4-METHOXYCYCLOBRASSININ, A SULFUR-CONTAINING PHYTOALEXIN ISOLATED FROM TURNIP BRASSICA-CAMPESTRIS L SSP RAPA
K MONDE, K TAMURA, M TAKASUGI, K KOBAYASHI, M SOMEI, HETEROCYCLES, 38, 2, 263, 267, Feb. 1994
English, Introduction scientific journal

Active Defense Mechanisms in Plants- Structureand Biosynthesis of Cruciferous Phytoalexins
MONDE Kenji, 化学と工業 = Chemistry and chemical industry, 45, 2, 295, 299, 01 Feb. 1992
日本化学会, Japanese

機器分析ハンドブック２ 高分子・分離分析編
床波 志保, 前田 耕治, 安川 智之, 10章 旋光度と円偏光二色法（CD）
化学同人, Oct. 2020, 9784759820225, vii, 177p, 140-153, Japanese, [Contributor]

化学便覧 基礎編 改訂6版　　　　　　　　　　　　　　　
日本化学会, 15章 分光学的性質 ―生体物質の円二色性―
丸善出版㈱, 2020, 9784621097243, 97-98, Japanese, [Contributor]

セラミド研究の新展開 ～基礎から応用へ～　　　　　　　　　　　　　　　
セラミド研究会, 第33章 ”天然物を利用したセラミド関連物質の化学合成戦略”
食品化学新聞社, 2019, 9784916143358, 337, 278-285, Japanese, Scholarly book, [Contributor]

キラル化学 : その起源から最新のキラル材料研究まで（CSJ Current Review, 13）
日本化学会, Chap 2 ”赤外円二色スペクトルによる絶対配置決定”
化学同人, 2013, 9784759813739, 43-49, Japanese, [Contributor]

「赤外円二色性スペクトル法における新展開」　　　　　　　　　　　　　　　
門出 健次
高分子, 2012, 779-780

Comprehensive Chiroptical Spectroscopy
Berova Nina
John Wiley & Sons, 2011, 9780470641354

高分子分析技術最前線
高分子学会
共立出版, 2007, 9784320043794, Japanese

「第五版実験化学講座,１４巻, 有機化合物の合成（Ⅱ）」　　　　　　　　　　　　　　　
丸善株式会社, 2005

糖鎖生物学入門
Taylor Maureen, Drickamer Kurt 著, 西村 紳一郎, 門出 健次
化学同人, 2005, 9784759810356, Japanese

「植物病害の化学」　　　　　　　　　　　　　　　
学会出版センター, 1997

「２４章第３節第４項 絶対立体配置」, 有機合成実験法ハンドブック 第２版　　　　　　　　　　　　　　　
門出 健次
丸善出版

はじめての生命科学　　　　　　　　　　　　　　　
北海道大学・総合教育部

生命有機化学　　　　　　　　　　　　　　　
北海道大学理学部 生物科学科（高分子機能学）

基礎高分子合成化学　　　　　　　　　　　　　　　
北海道大学理学部 生物科学科（高分子機能学）

有機化学演習　　　　　　　　　　　　　　　
北海道大学理学部 生物科学科（高分子機能学）

生命融合科学概論　　　　　　　　　　　　　　　
北海道大学・大学院生命科学院

生命物質科学特論　　　　　　　　　　　　　　　
北海道大学・大学院生命科学院

Jul. 2020 - Present
The Japanese Conference on the Chemistiry of Lipids　　　　　　　　　　　　　　　

未到の波長に突破口を切り拓く：短波赤外蛍光イメージングプローブの創出と応用
科学研究費助成事業
28 Jun. 2024 - 31 Mar. 2027
門出 健次, M.M Mahadeva・Swamy, 神 隆
日本学術振興会, 挑戦的研究(萌芽), 北海道大学, 24K21815

スフィンゴミエリン合成酵素２阻害剤による腫瘍免疫亢進を介した新規抗癌治療の開発
科学研究費助成事業
01 Apr. 2022 - 31 Mar. 2025
岡崎 俊朗, 村井 勇太, 谷口 真, 門出 健次
日本学術振興会, 基盤研究(B), 23K24187

スフィンゴミエリン合成酵素２阻害剤による腫瘍免疫亢進を介した新規抗癌治療の開発
科学研究費助成事業
01 Apr. 2022 - 31 Mar. 2025
岡崎 俊朗, 村井 勇太, 谷口 真, 門出 健次
日本学術振興会, 基盤研究(B), 石川県立大学, 22H02926

Development of novel stereochemical analytical technique of biomolecules by the VCD exciton chirality method
Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research (B)
Apr. 2019 - Mar. 2023
門出 健次, 谷口 透, 村井 勇太
赤外円二色性スペクトル（VCD）は、キラルな分子の立体構造を解析する分光法である。我々は「VCD励起子キラリティー」と命名した理論計算を必要としない最初の非経験的法則を見出している。本法はカルボニル基の二つの発色団の相互作用を基盤としており、極めて高感度である。本研究では、VCD励起子キラリティー法を１）アルキン、アジド、ニトリルなどの他のIR官能基に関しても適用可能であるか検証すること。２）本法を生体関連中分子等の立体構造解析へ適用すること。３）赤外円二色性スペクトル（VCD）と同様な振動分光であるキラルラマンスペクトル（ROA）での本法の展開性を検証することを目的としている。
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Hokkaido University, Principal investigator, 19H02836

The mechanistic study and pharmaceutical development of obesity suppressive natural product, Malabaricone isolated from Malaysian fruit
Grants-in-Aid for Scientific Research Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
Apr. 2020 - Mar. 2022
門出 健次
現在、我が国の死亡原因はガンに続き、心疾患、脳血管疾患が上位を占める。その要因は主として脂質代謝疾患による脂質蓄積の異常が原因であると考えられている。脂質合成酵素の内、スフィンゴミエリン合成酵素(SMS)は、その阻害により、ガン免疫亢進、アミロイドβのクリアランス等に効果があることが知られている。我々は、フルーツより得られたマラバリコーンが高いSMS阻害能及び肥満抑制効果を有することを見出している。しかし、マラバリコーンによる肥満抑制効果についての詳細な分子機構は明らかとなっていない。本研究では、この分子機構を明らかにすることにより、ガン、肥満抑制に関する機構の情報を得ること目的としている。
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area), Hokkaido University, Principal investigator, 20H04756

Study for molecules initiated lipid related disease biomarkers
Grants-in-Aid for Scientific Research Challenging Research (Exploratory)
Jun. 2017 - Mar. 2020
Monde Kenji
L-serine, the head part of a sphingosine, is incorporated by serine palmitoyl transferase (SPT）, coupled with a palmitoyl CoA in the first stage of its biosynthesis and converted into ceramides. Recently, it has been suggested that not only L-serine but also other amino acids may be incorporated into this biosynthetic system, and its association with lipid-related diseases has been trend. We have been succeeded in synthesizing sphingosines having phenylalanine, alanine, tryptophan, leucine, cysteine, and threonine in its head part for the purpose of providing authentic standard samples in a mass spectrometric analysis. We also constructed a unique ceramide library by binding some of these to fatty acids. It was found that some of them showed inhibitory activity of sphingomyelin synthase.
Japan Society for the Promotion of Science, Challenging Research (Exploratory), Hokkaido University, Principal investigator, 17K19188

ポリエステル系ペプチドミミックを指向したVCDによるバイオポリマー立体構造解析法　　　　　　　　　　　　　　　
基盤研究(B)
Apr. 2015 - Mar. 2018
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

理論計算を必要としない赤外円二色性スペクトルによる新規絶対配置決定法の開発　　　　　　　　　　　　　　　
基盤研究(B)
Apr. 2012 - Mar. 2015
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

先端融合領域イノベーション創出拠点の形成　　　　　　　　　　　　　　　
未来創薬・医薬イノベーション拠点形成
2006 - 2015
山口 佳三
科学技術振興機構（文部科学省）, Competitive research funding

フードイノベーション創造支援事業（札幌市補助事業）　　　　　　　　　　　　　　　
実証研究支援補助金
2014
門出 健次
札幌市, Principal investigator, Competitive research funding

赤外円二色法による迅速高次構造解析と三次元化合物ライブラリの構築
科学研究費助成事業
2011 - 2013
門出 健次, CHANNAPILLE Kopp
本研究では、特別研究員のこれまでの合成技術により合成した化合物を合成し、立体化学研究をVCD法により遂行、新規キラルドラッグライク化合物ライブラリの構築することを目的としている。本年度は生理活性物質として、スフィンゴシンにしぼった。スフィンゴシンは、疎水性、親水性の両方性質をもつため取扱いが困難である。そのため、昨年に引き続きスフィンゴシン補足樹脂の合成と最適化を実施した。スフィンゴシン補足樹脂作成のため、グルタルアルデヒド誘導体の大量合成を実施した。また、樹脂に関しても複数種類を入手し、カップリングにより補足樹脂の最適化を試みたが、当面、従来法の樹脂が最適であるとの結論を得た。また、ファイトスフィンゴシンに対しても補足、リリースの最適化を行った。樹脂は、ファイトスフィンゴシン類に関しても有効であることが判明した。更に、多様性化合物の確保をめざして、天然資源からの簡便抽出法の開発を試みた。サンプルとして、タモギダケを選び、これからグルコセラミドを大量に単離、標準サンプルとした。糖鎖の加水分解を実施したが、反応の進行が困難であったので、詳細な加水分解の条件検討を実施した。また、別途合成されたスフィンゴシン誘導体を用いて、2位のアミノ基に対して、研究室保有のカルボン酸ライブラリのアミド化反応による多種類化合物の調整を試みた。特に、多種類のカルボン酸に対して、容易かつ確実に進行する条件を検討した。また、合成した光学活性生理活性物質に関して、単離することなく、プレート上での生理活性試験を実施した。脂質関係酵素を含む細胞系と蛍光ラベル基質を用いたアッセイ系での活性測定を試みた。その結果、一部について活性が認められた。
日本学術振興会, 特別研究員奨励費, 北海道大学, 11F01334

官能基特異的反応に着目したスフィンゴシン類の選択的捕捉法の開発　　　　　　　　　　　　　　　
挑戦的萌芽研究
2011 - 2013
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

赤外円二色性スペクトルによる分子キラル分析法の開発　　　　　　　　　　　　　　　
研究助成金
2010 - 2013
門出 健次
財団法人篷庵社, Principal investigator, Competitive research funding

さっぽろバイオクラスター構想 ”Bio-S”　　　　　　　　　　　　　　　
知的クラスター創成事業（第II期）
2007 - 2011
鈴木 文夫
文部科学省, Competitive research funding

赤外円二色法によるスタンダード・キロプティカル構造解析法の構築　　　　　　　　　　　　　　　
基盤研究(B)
2008 - 2010
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

生物によるキラル円偏光識別とその分子機構の解明　　　　　　　　　　　　　　　
挑戦的萌芽研究
2008 - 2010
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

疾患早期診断のための糖鎖自動分析装置開発　　　　　　　　　　　　　　　
先端計測分析技術機器・開発事業
2004 - 2008
西村 紳一郎
科学技術振興機構（文部科学省）, Competitive research funding

弱い相互作用に着目した機能性天然物の高速探索　　　　　　　　　　　　　　　
萌芽研究
2005 - 2007
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

赤外領域円二色性スペクトルによるキラル分析法の応用研究　　　　　　　　　　　　　　　
基盤研究(B)
2004 - 2007
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

不凍糖タンパク質の生理機能を活用する臓器・細胞保存剤の開発　　　　　　　　　　　　　　　
地域コンソーシアム研究開発事業
2004 - 2005
西村 紳一郎
経済産業省, Competitive research funding

Photocontrol of ion flux across a lipid bilayer membrane by visible light
Grants-in-Aid for Scientific Research
2003 - 2005
JIN Takashi, MONDE Kenji
Lipid bilayer membranes that respond to light are of great interest for the development of the artificial visual systems for use in optoelectronic devices and optical transducers. There are many studies of the photocontrol of ion transport across lipid bilayer membranes using photoresponsive compounds such as amphiphilic azobenzene and spirobenzopyran derivatives. Most of the studies have used changes in membrane capacitance due to the disruption of lipid bilayer structures, which results from the photoisomerization of the compounds incorporated into the lipid bilayers. So far, several groups have reported photocontrollable ion transport systems, where channel or carrier molecules attaching photochromic compounds were incorporated into lipid bilayer membranes. In these systems, photochromic reaction has been conducted by irradiation of UV light (300-380nm). The prolonged UV irradiation, however, usually results in photodamage to photochromic compounds and lipid molecules.
In the present study, we have chosen calix[4]arene as a basic skeleton of a photoresponsive ion carrier because its ether derivatives are known to act as Na^+ ion carriers in lipid bilayer membranes. For the synthesis of a photoresponsive carrier, dimethylaminoazobenzene was introduced as a photochromic compound to an ether derivative of p-tert-butylcalix[4]arene. Among azobenzene derivatives, dimethylaminoazobenzene has an intense absorption in the visible region, which is attributed to the π-π* transition of the trans isomer. We expected that the dimethylaminoazobenzene appended calix[4]arene derivative mediates Na^+ ion transport across a lipid bilayer membrane, and the ion transport ability can be controlled by irradiation of visible light. In this study, we have succeeded to develop a visible light-driven ion transport system using a calix[4]arene-based photoresponsive ion carrier, where Na^+ flux across a lipid bilayer can be controlled by irradiation of light (>400nm).
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (C), HOKKAIDO UNIVERSITY, 15550142

糖鎖自動合成装置における反応モニタリング技術の開発　　　　　　　　　　　　　　　
糖鎖エンジニアリングプロジェクト/糖鎖構造解析技術開発
2003 - 2005
西村 紳一郎
経済産業省, Competitive research funding

人工細胞外マトリックスの精密分子設計と靭帯および関節軟骨細胞再生への応用　　　　　　　　　　　　　　　
基盤研究(B)
2003 - 2005
眞島 任史
文部科学省科学研究費, Competitive research funding

複合糖鎖データベースリーディングプロジェクト　　　　　　　　　　　　　　　
新世紀重点研究創成プラン（ＲＲ）
2003 - 2004
西村 紳一郎
文部科学省, Competitive research funding

複合糖質の新規キラル分析法の開発　　　　　　　　　　　　　　　
萌芽研究
2002 - 2004
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

北方系植物資源データベースの構築及び抽出物ライブラリの整備　　　　　　　　　　　　　　　
一次産品活用型バイオベンチャー育成支援調査
2004
門出 健次
国土交通省, Principal investigator, Competitive research funding

機能性糖鎖複合材料創製技術開発　　　　　　　　　　　　　　　
大学連携産業科学技術研究開発プロジェクト
1999 - 2003
西村 紳一郎
経済産業省, Competitive research funding

New Strategy for Determining the Absolute Stereochemistry of Mono-Functional Natural Products by the CD Exciton Chirality Method
Grants-in-Aid for Scientific Research
1999 - 2002
HARADA Nobuyuki, MATSUMOTO Takatoshi, WATANABE Masataka
1. We have developed a new strategy for determining the absolute configuration of mono-fucntional compounds by the CD exciton chirality method. This method is powerful for the absolute configurational studies of chiral compounds including natural products.
2. We have recently developed two "powerful chiral acids" for enantioresolution of various alcohols by HPLC on silica gel and also for determination of their absolute configurations by X-ray crystallography and/or by the 1H NMR anisotropy method. The first is the chiral dichlorophthalic acid (-)-1, which was reacted with racemic alcohol to give a diastereomeric mixture of esters. The mixture of esters obtained was separated by HPLC on silica gel, and two separated esters were crystallized respectively to afford single crystals suitable for X-ray analysis. The absolute configuration of the alcohol part was determined by X-ray crystallography of the esters, and enantiopure alcohols were easily recovered by solvolysis with K_2CO_3 in methanol.
3. The second powerful chiral acid is 2-methoxy-2-(1-naphthyl)propionic acid (MαNP acid, (S)-(+)-2 or R-(-)-2) for determining the absolute configuration of chiral alcohols by the 1H NMR anisotropy method.The enantiopure MαNP acid (S)-(+)-2 was allowed to react with racemic alcohols yielding diastereomeric mixtures of esters, which were easily separated by HPLC on silica gel. The NMR signals of diastereomeric esters obtained were fully assigned by the various two-dimensional methods leading to the calculation of Δδ values (Δδ = δ(R,X)-δ(S,X)). By applying the MαNP sector rule, the absolute configuration X was determined. Separated esters were hydrolyzed with KOH/EtOH to recover enantiopure alcohols.
4. Using MαNP acid, (S)-(+)-2 and its deuterium labeled enantiomer R-(-)-2-d_6, we have developed a new diastereomer method for determining enantiomeric excess (% ee) of chiral alcohols by MS spectrometry.
Japan Society for the Promotion of Science, Grant-in-Aid for Scientific Research (B), Tohoku University, 11480159

コンピュータを用いた生物有機資源からの消化抑制剤等の開発　　　　　　　　　　　　　　　
即効型地域新生コンソーシアム研究開発事業
2002
門出 健次
経済産業省, Principal investigator, Competitive research funding

色覚に関与する視物質のモデル化合物による解析　　　　　　　　　　　　　　　
奨励研究(A)
1999 - 2000
門出 健次
文部科学省科学研究費, Principal investigator, Competitive research funding

Pacifichem2000渡航費用　　　　　　　　　　　　　　　
2000
門出 健次
栗林育英学術財団, Principal investigator, Competitive research funding

フッ素ラベルリガンドとレセプターとの相互作用に関する研究　　　　　　　　　　　　　　　
奨励研究(A)
1997 - 1998
門出 健次
文部省・科学研究費, Principal investigator, Competitive research funding

在外研究員（若手）
Mar. 1994 - Dec. 1994
門出 健次
文部省, Principal investigator, Competitive research funding

アブラナ科植物のファイトアレキシンの生成機構
科学研究費助成事業
1994 - 1994
高杉 光雄, 門出 健次
1.アブラナ科植物のファイトアレキシンの産生を誘導する内因性エリシターの探索
カブを大根おろし状とし、おろし汁を除去、洗浄したカブ繊維状組織を滅菌水に懸濁し、紫外線を照射した後、水層に滲出してくる物質にエリシター活性を認めた。透析により分子量約1000以上の不活性部を除き、ファイトアレキシンcyclobrassininの生成量をエリシター活性の指標として各種クロマトグラフィーにより分離し、酸性糖質分画に活性を認めた。
2.cyclobrassinin生合成経路の検討
cyclobrassininがmethoxybrassininを経由するか、あるいはbrassininから直接生成するか検討した。重水素標識brassininを投与した後、単離したcyclobrassininとmethoxybrassininについて重水素標識の取り込を調査したところ、cyclobrassininには取り込まれたもののmethoxybrassininには全く取り込まれていなかった。また重水素標識methoxybrassininの投与により得たcyclobrassininにも重水素標識が全く取り込まれないことも確認した。従って、cyclobrassininはmethoxybrassininを経由しないで生合成される。
3.brassicanal Aの生合成研究
紫外線照射により活性化したカブスライスに、生体異物であるアセトアニリドを投与したところ、アセトアニリド由来のアニリンがbrassicanal Aの生合成中間体をトラップした構造の生成物を得た。これより、cyclobrassininより生成するdehydrobrassininの加水分解生成物、3-formyl-2-mercaptoindoleのメチル化によりbrassicanal Aが生合成されると推定した。
日本学術振興会, 一般研究(C), 北海道大学, 06660125

シロイヌナズナのファイトアレキシン及びその生合成研究　　　　　　　　　　　　　　　
奨励研究(A)
1993
門出 健次
文部省・科学研究費, Principal investigator, Competitive research funding

18th IUPAC International Symposium on the Chemistry of Natural Products渡航費用　　　　　　　　　　　　　　　
1992
門出 健次
実吉財団, Principal investigator, Competitive research funding

アブラナ科植物ファイトアレキシンの生合成研究　　　　　　　　　　　　　　　
奨励研究(A)
1992
門出 健次
文部省・科学研究費, Principal investigator, Competitive research funding

アブラナ科植物の産生する新規含硫ファイトアレキシンの生物有機化学的研究　　　　　　　　　　　　　　　
一般研究(B)
1988 - 1990
高杉 光雄
文部省・科学研究費, Competitive research funding

電荷移動プロセスとひずみ結合の反応性　　　　　　　　　　　　　　　
一般研究(C)
1990
平尾 健一
文部省・科学研究費, Competitive research funding

ヒラタケ病原菌の生理活性物質に関する研究　　　　　　　　　　　　　　　
教育研究学内特別経費
1990
門出 健次
北海道大学, Principal investigator, Competitive research funding

ヒラタケ病原細菌の生産する生理活性物質に関する生物有機化学的研究　　　　　　　　　　　　　　　
1990
門出 健次
秋山記念生命科学振興財団, Principal investigator, Competitive research funding

17th IUPAC International Symposium on the Chemistry of Natural Products渡航費用　　　　　　　　　　　　　　　
1990
門出 健次
薬学振興財団, Principal investigator, Competitive research funding

細菌感染により誘導されるキク科食用植物の抗菌活性物質の生物有機化学的研究　　　　　　　　　　　　　　　
奨励研究(A)
1989
門出 健次
文部省・科学研究費, Principal investigator, Competitive research funding

Chiral analysis of glycoconjugates by Vibrational Circular Dichroism (VCD)　　　　　　　　　　　　　　　
Competitive research funding