Researcher Database

Murai Yuta
Faculty of Advanced Life Science Functional Life Sciences Glyco-signal Biology
Assistant Professor

Researcher Profile and Settings

Affiliation

  • Faculty of Advanced Life Science Functional Life Sciences Glyco-signal Biology

Job Title

  • Assistant Professor

Research funding number

  • 20707038

ORCID ID

J-Global ID

Research Interests

  • infertility treatment   sphingolipid   Alzheimer's disease   生物有機化学   光アフィニティーラベル法   ケミカルバイオロジー   

Research Areas

  • Life sciences / Bioorganic chemistry

Academic & Professional Experience

  • 2020/05 - Today 理化学研究所 客員研究員
  • 2013/08 - Today Hokkaido University Faculty of Advanced Life Science
  • 2013/04 - 2013/07 Ritsumeikan University

Education

  • 2010/04 - 2013/03  Hokkaido University  Graduate School of Agriculture

Research Activities

Published Papers

  • Yuta Murai, Kohei Yuyama, Daisuke Mikami, Yasuyuki Igarashi, Kenji Monde
    Chemistry and physics of lipids 245 105202 - 105202 2022/03/22 
    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.
  • Yuta Murai, Akihiro Sekiguchi, Taeko Hirakawa, Seigo Usuki, Yasuyuki Igarashi, Kenji Monde
    Chirality 2022/03/16 
    Neuropathic pain is an unbearable condition caused by nervous system damage. As distinct acute pain, neuropathic pain is chronic, and it severely influences quality of life. N,N-Dimethyl-d-erythro-sphingosine (DMS), a neuropathic pain inducer, is metabolited de novo from sphingosine. In a recent study, metabolomics showed an increased concentration level of DMS in the spinal cord in mice with neuropathic pain. Nerve growth factor (NGF) is one of the peripheral nervous system targeted pain factors that interact with tropomyosin receptor kinase A (trkA). On the basis of this information, we were interested in the possibility that DMS may induce neuropathic pain-like behavior through an increase of NGF activity. In this study, we showed that DMS can enhance the binding of NGF to trkA, followed by neurite outgrowth of epidermal nerve fibers and phosphorylation of trkA. In addition, a stereoisomer, N,N-dimethyl-l-erythro-sphingosine, did not any show such biological activities. The results suggest that DMS can enhance the binding of NGF to trkA and that its stereochemistry is an essential factor for exhibiting its activity.
  • Yuta Murai, Makoto Hashimoto, Takuma Yoshida, Zetryana Puteri Tachrim
    HETEROCYCLES 104 (1) 167 - 167 0385-5414 2022
  • Mahadeva M M Swamy, Yuta Murai, Kenji Monde, Setsuko Tsuboi, Takashi Jin
    Bioconjugate chemistry 32 (8) 1541 - 1547 2021/08/18 
    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.
  • Zetryana Puteri Tachrim, Lei Wang, Yuta Murai, Makoto Hashimoto
    Molecules (Basel, Switzerland) 26 (15) 2021/07/26 
    This review focuses on diaziridine, a high strained three-membered heterocycle with two nitrogen atoms that plays an important role as one of the most important precursors of diazirine photoaffinity probes, as well as their formation and transformation. Recent research trends can be grouped into three categories, based on whether they have examined non-substituted, N-monosubstituted, or N,N-disubstituted diaziridines. The discussion expands on the conventional methods for recent applications, the current spread of studies, and the unconventional synthesis approaches arising over the last decade of publications.
  • Makoto Hashimoto, Manami Hashinoki, Natsumi Kurokawa, Yuta Murai, Zetryana Puteri Tachrim, Yasuko Sakihama, Takeyuki Suzuki
    HETEROCYCLES 103 (1) 392 - 392 0385-5414 2021
  • 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 - 4077 2020/09/07 
    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.
  • Sajeer Koolath, Yuta Murai, Yoshiko Suga, Kenji Monde
    Chirality 32 (3) 308 - 313 2020/03 [Refereed][Not invited]
     
    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.
  • 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) 2020/02/24 [Refereed][Not invited]
     
    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
    Eur. J. Org. Chem. 7563 - 7567 2019/11 [Refereed][Not invited]
  • 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 2019/08/08 [Refereed][Not invited]
     
    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.
  • Yasuyuki Hashidoko, Hiroaki Nishizuka, Manato Tanaka, Kanako Murata, Yuta Murai, Makoto Hashimoto
    Scientific reports 9 (1) 4751 - 4751 2019/03/18 [Refereed][Not invited]
     
    Coralloid roots are specialized tissues of cycads (Cycas revoluta) that are involved in symbioses with nitrogen-fixing Nostoc cyanobacteria. We found that a crude methanolic extract of coralloid roots induced differentiation of the filamentous cell aggregates of Nostoc species into motile hormogonia. Hence, the hormogonium-inducing factor (HIF) was chased using bioassay-based isolation, and the active principle was characterized as a mixture of diacylglycerols (DAGs), mainly composed of 1-palmitoyl-2-linoleoyl-sn-glycerol (1), 1-palmitoyl-2-oleoyl-sn-glycerol (2), 1-stearoyl-2-linolenoyl-sn-glycerol (3), and 1-stearoyl-2-linoleoyl-sn-glycerol (4). Enantioselectively synthesised compound 1 showed a clear HIF activity at 1 nmol (0.6 µg) disc-1 for the filamentous cells, whereas synthesised 2-linoleoyl-3-palmitoyl-sn-glycerol (1') and 1-palmitoyl-2-linoleoyl-rac-glycerol (1/1') were less active than 1. Conversely, synthesised 1-linoleoyl-2-palmitoyl-rac-glycerol (8/8') which is an acyl positional isomer of compound 1 was inactive. In addition, neither 1-monoacylglycerols nor phospholipids structurally related to 1 showed HIF-like activities. As DAGs are protein kinase C (PKC) activators, 12-O-tetradecanoylphorbol-13-acetate (12), urushiol C15:3-Δ10,13,16 (13), and a skin irritant anacardic acid C15:1-Δ8 (14) were also examined for HIF-like activities toward the Nostoc cells. Neither 12 nor 13 showed HIF-like activities, whereas 14 showed an HIF-like activity at 1 nmol/disc. These findings appear to indicate that some DAGs act as hormogonium-inducing signal molecules for filamentous Nostoc cyanobacteria.
  • 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 2019/02/22 [Refereed][Not invited]
     
    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.
  • 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 1359-7345 2018/11/08 [Refereed][Not invited]
     
    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.
  • 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 2018/01/31 [Refereed][Not invited]
     
    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.
  • Yuta Murai, Lei Wang, Makoto Hashimoto
    Photoaffinity Labeling for Structural Probing Within Protein 111 - 128 2017/09/25 [Refereed][Not invited]
     
    As photophores in photoaffinity labeling, three major types, arylazide, benzophenone, and diazirine have been used and contributed to the understanding of molecular biology processes. In particular, diazrine is a significantly useful photophore because it has some advantages such as its relatively small size, stability, low rate of rearrangement, and generating a high reactive carbene with longer wavelength which reduces damage to the target molecules. Nevertheless, despite these many advantages in diazirine, there are reports in which arylazide and benzophenone are generally utilized for photoaffinity labeling compared with diazirine due to its synthetic difficulty onto ligands. To overcome this problem, recently many researchers have addressed to establish the efficient synthetic route of diazirinyl compounds. Particularly, a-aromatic amino acids possess not only biological activities themselves but also basic component of protein (bioactive peptide). In addition, a number of heterocyclic bioactive compounds have variety of attractive biological activities. Therefore, their diazirinyl compounds promise the molecular biology processes. In this chapter, firstly, it is demonstrated the simple and efficient preparation of diazirine on aromatics and aliphatic chains. Furthermore post-functional derivatization of them is also described to diversify bioactive compounds.
  • Zetryana Puteri Tachrim, Lei Wang, Yuta Murai, Takuma Yoshida, Natsumi Kurokawa, Fumina Ohashi, Yasuyuki Hashidoko, Makoto Hashimoto
    CATALYSTS 7 (2) 2073-4344 2017/02 [Refereed][Not invited]
     
    Trifluoromethanesulfonic acid (TfOH) is one of the superior catalysts for acylation. The catalytic activity of TfOH in C- and/or O-acylation has broadened the use of various substrates under mild and neat or forced conditions. In this review, the salient catalytic features of TfOH are summarized, and the unique controllability of its catalytic activity in the tendency of C-acylation and/or O-acylation is discussed.
  • 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 (6) 1045 - 1051 1434-193X 2017/02 [Refereed][Not invited]
     
    Fluorous solid-phase extraction (FSPE) is a useful technique for efficient selective enrichment of fluorous compounds from nonfluorous molecules. Sphingolipids and their metabolites, which are ubiquitous building blocks of eukaryotic and prokaryotic cell membranes, play crucial roles, for example, as signaling molecules. However, details of the functions and metabolic mechanisms of exogenous sphingolipids have remained unknown compared with those of their endogenous analogs. To better understand these unknown roles, chemical probes with appropriate biological and physicochemical properties are needed. In this study, we designed and synthesized new fluorous sphingolipids to reveal these roles. Furthermore, we confirmed that they could be efficiently and rapidly separated from normal sphingolipids by FSPE, and that they hardly showed any cytotoxic activity, similarly to normal sphingolipids at the same dose. We also showed that these fluorinated ceramides could act as metabolic substrates for sphingomyelin synthase 2 (SMS2). This demonstrates their potential for further biological studies.
  • 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 [Not refereed][Not invited]
  • Mengcen Wang, Seiji Tachibana, Yuta Murai, Li Li, Sharon Yu Ling Lau, Mengchao Cao, Guonian Zhu, Makoto Hashimoto, Yasuyuki Hashidoko
    Scientific reports 6 26217 - 26217 2045-2322 2016/05/20 [Refereed][Not invited]
  • Atsufumi Nakahashi, Ananda Kumar C Siddegowda, Mostafa A S Hammam, Siddabasave Gowda B Gowda, Yuta Murai, Kenji Monde
    Organic letters 18 (10) 2327 - 30 1523-7060 2016/05/20 [Refereed][Not invited]
     
    Vibrational circular dichroism (VCD) was first applied to the stereochemical analysis of sphingosine. VCD patterns derived from the C═C stretch as well as other mid-infrared (IR) regions were practical markers to discriminate all the stereoisomers of intact sphingosine. Glutaraldehyde was found as an excellent derivatizing reagent for sphingosine which improves its solubility in VCD-friendly nonpolar solvents such as chloroform and enhances the VCD intensities by forming a rigid cyclized structure.
  • Yuta Murai, Takuma Yoshida, Lei Wang, Katsuyoshi Masuda, Yasuyuki Hashidoko, Kenji Monde, Yasumaru Hatanaka, Makoto Hashimoto
    SYNLETT 27 (6) 946 - 950 0936-5214 2016/04 [Refereed][Not invited]
     
    5-Nitro-2-propoxyaniline is one of the strongest artificial sweeteners. However, little is known about the detailed relationship of the structure and biological activity between 5-nitro-2-propoxyaniline and its sweet receptor. Photoaffinity labeling is a useful method for revealing interactions of a small bioactive compound with molecules. Therefore, we synthesized photoreactive 2-propoxyaniline derivatives as useful tools for revealing the interactions by photoaffinity labeling.
  • Mengcen Wang, Seiji Tachibana, Yuta Murai, Li Li, Sharon Yu Ling Lau, Mengchao Cao, Guonian Zhu, Makoto Hashimoto, Yasuyuki Hashidoko
    Scientific reports 6 22596 - 22596 2016/03/03 [Refereed][Not invited]
     
    Burkholderia heleia PAK1-2 is a potent biocontrol agent isolated from rice rhizosphere, as it prevents bacterial rice seedling blight disease caused by Burkholderia plantarii. Here, we isolated a non-antibacterial metabolite from the culture fluid of B. heleia PAK1-2 that was able to suppress B. plantarii virulence and subsequently identified as indole-3-acetic acid (IAA). IAA suppressed the production of tropolone in B. plantarii in a dose-dependent manner without any antibacterial and quorum quenching activity, suggesting that IAA inhibited steps of tropolone biosynthesis. Consistent with this, supplementing cultures of B. plantarii with either L-[ring-(2)H5]phenylalanine or [ring-(2)H2~5]phenylacetic acid revealed that phenylacetic acid (PAA), which is the dominant metabolite during the early growth stage, is a direct precursor of tropolone. Exposure of B. plantarii to IAA suppressed production of both PAA and tropolone. These data particularly showed that IAA produced by B. heleia PAK1-2 disrupts tropolone production during bioconversion of PAA to tropolone via the ring-rearrangement on the phenyl group of the precursor to attenuate the virulence of B. plantarii. B. heleia PAK1-2 is thus likely a microbial community coordinating bacterium in rhizosphere ecosystems, which never eliminates phytopathogens but only represses production of phytotoxins or bacteriocidal substances.
  • Siddabasave Gowda B Gowda, Seigo Usuki, Mostafa A S Hammam, Yuta Murai, Yasuyuki Igarashi, Kenji Monde
    Journal of lipid research 57 (2) 325 - 31 0022-2275 2016/02 [Refereed][Not invited]
     
    Sphingoid base derivatives have attracted increasing attention as promising chemotherapeutic candidates against lifestyle diseases such as diabetes and cancer. Natural sphingoid bases can be a potential resource instead of those derived by time-consuming total organic synthesis. In particular, glucosylceramides (GlcCers) in food plants are enriched sources of sphingoid bases, differing from those of animals. Several chemical methodologies to transform GlcCers to sphingoid bases have already investigated; however, these conventional methods using acid or alkaline hydrolysis are not efficient due to poor reaction yield, producing complex by-products and resulting in separation problems. In this study, an extremely efficient and practical chemoenzymatic transformation method has been developed using microwave-enhanced butanolysis of GlcCers and a large amount of readily available almond β-glucosidase for its deglycosylation reaction of lysoGlcCers. The method is superior to conventional acid/base hydrolysis methods in its rapidity and its reaction cleanness (no isomerization, no rearrangement) with excellent overall yield.
  • Lei Wang, Takuma Yoshida, Yasuyuki Muto, Yuta Murai, Zetryana Puteri Tachrim, Akiko Ishida, Shiori Nakagawa, Yasuko Sakihama, Yasuyuki Hashidoko, Katsuyoshi Masuda, Yasumaru Hatanaka, Makoto Hashimoto
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (14) 3129 - 3134 1434-193X 2015/05 [Refereed][Not invited]
     
    Saccharin is one of the most common artificial sweeteners that has a bitter taste at high concentrations. Currently, there are no detailed functional analyses of these gustatory receptors. Therefore, we designed and synthesized photoreactive saccharin derivatives that contain a (trifluoromethyl) diazirinyl moiety at the 5- or 6-position for use as functional analysis tools for photoaffinity labeling.
  • Lei Wang, Yuta Murai, Takuma Yoshida, Akiko Ishida, Katsuyoshi Masuda, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, Makoto Hashimoto
    ORGANIC LETTERS 17 (3) 616 - 619 1523-7060 2015/02 [Refereed][Not invited]
     
    Alternative one-pot synthesis of 3-(trifluoromethyl)-3-phenyldiazirine derivatives from corresponding tosyloximes is developed. The deprotonation of intermediate diaziridine by NH2- is a new approach for construction of diazirine. Moreover, a novel synthesis of optically pure (trifluoromethyl)diazirinylphenylalanine derivatives was attempted involving these methods.
  • Munenori Sakurai, Takuma Yoshida, Lei Wang, Yuta Murai, Katsuyoshi Masuda, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, Makoto Hashimoto
    HETEROCYCLES 90 (1) 698 - 705 0385-5414 2015/01 [Refereed][Not invited]
     
    Salicin (salicyl alcohol glucoside) is a substance well known for its bitter taste. A photoreactive diazirinyl derivative of salicin will be utilized for the functional analysis of interactions between the bitter taste receptor and salicin. Glucosides of salicyl derivatives are more difficult than phenol derivatives that are unsubstituted at the ortho-position. A diazirinyl salicin derivative was synthesized at moderate yields by glucosidation of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl bromide and 2-hydroxy-4-[3-(trifluoromethyl)-3H-diazirin-3-yl]benzaldehyde in the presence of a phase-transfer catalyst, nBuEt(3)NBr, followed by reduction and deprotection.
  • Lei Wang, Yuta Murai, Takuma Yoshida, Masashi Okamoto, Katsuyoshi Masuda, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, Makoto Hashimoto
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 78 (7) 1129 - 1134 0916-8451 2014/07 [Refereed][Not invited]
     
    In this paper we report here a hydrogen/deuterium exchange (H/D exchange) of cross-linkable alpha-amino acid derivatives with deuterated trifluoromethanesulfonic acid (TfOD). H/D exchange with TfOD was easily applied to o-catechol containing phenylalanine (DOPA) within an hour. A partial H/D exchange was observed for trifluoromethyldiazirinyl (TFMD) phenylalanine derivatives. N-Acetyl-protected natural aromatic alpha-amino acids (Tyr and Trp) were more effective in H/D exchange than unprotected ones. The N-acetylated TFMD phenylalanine derivative afforded slightly higher H/D exchange than unprotected derivatives. An effective post-deuteration method for cross-linkable alpha-amino acid derivatives will be useful for the analysis of biological functions of bioactive peptides and proteins by mass spectrometry.
  • Lei Wang, Yuta Murai, Takuma Yoshida, Masashi Okamoto, Zetryana Puteri Tachrim, Yasuyuki Hashidoko, Makoto Hashimoto
    MOLECULES 19 (5) 6349 - 6367 1420-3049 2014/05 [Refereed][Not invited]
     
    Aryl-keto-containing alpha-amino acids are of great importance in organic chemistry and biochemistry. They are valuable intermediates for the construction of hydroxyl alpha-amino acids, nonproteinogenic alpha-amino acids, as well as other biofunctional components. Friedel-Crafts acylation is an effective method to prepare aryl-keto derivatives. In this review, we summarize the preparation of aryl-keto containing alpha-amino acids by Friedel-Crafts acylation using acidic alpha-amino acids as acyl-donors and Lewis acids or Bronsted acids as catalysts.
  • Makoto Hashimoto, Yuta Murai
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN 72 (4) 360 - 369 0037-9980 2014/04 [Refereed][Not invited]
     
    Photoaffinity labeling is one of the favorite methods for chemical biology. The first step in this method is the construction of photophores and their modification to the associated high affinity target ligand. alpha-Amino acids have biological activities themselves and are fundamental component of peptides and protein. The photoreactive aromatic alpha-amino acids are useful for investigation of biological phenomenon. Although synthesis of photoreactive phenylalanine analogues has already been reported, there have been few reports of the synthesis of photoreactive tryptophan and side-chain elongated phenylalanine. We report here the effective photoreactive tryptophan and side-chain elongated phenylalanine derivatives. Furthermore, we report the mild and controllable hydrogen-deuterium exchange for aromatic hydrogen with trifluoromethanesulfonic acid-d during the course of the synthesis of side-chain elongated phenylalanine. These hydrogen-deuterium exchange properties for these aromatic alpha-amino acids are identical to those of the peptides. With this method the exchange proceeds significantly faster than previously described methods. Detail analysis of the exchange revealed that the method was controllable by temperature-, time-, and dose- dependent manner.
  • Sakurai, Munenori, Masuda, Katsuyoshi, Wang, Lei, Murai, Yuta, Sakihama, Yasuko, Hashidoko, Yasuyuki, Hatanaka, Yasumaru, Hashimoto, Makoto
    HETEROCYCLES 88 (1) 629 - 637 0385-5414 2014/01 [Refereed][Not invited]
     
    Photoreactive phenylalanine derivatives are well known as functional analysis reagents for target biomolecules. The photophores are commonly introduced at 4-position on benzene. Aspartame, which consists of dipeptide L-Asp-L-Phe-OMe, is one of the most utilized artificial sweeteners, and substitution effects on its benzene ring have been reported. Substitution at the 4-position, however, does not maintain its sweetness properties. Trifluoromethyldiazirine, which is one of the most reliable photophores, was introduced to a different site on phenylalanine and the new photoreactive phenylalanine was converted to aspartame derivatives. The new aspartame derivative had slightly higher sweetness potency than sucrose standard solution.
  • Yuta Murai, Lei Wang, Yasuyuki Muto, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, Makoto Hashimoto
    HETEROCYCLES 87 (10) 2119 - 2126 0385-5414 2013/10 [Refereed][Not invited]
     
    Simple and stereocontrolled preparation of benzoylated phenylalanine derivatives from optically pure phenylalanine using Friedel-Crafts reaction in trifluoromethanesulfonic acid (TfOH) is reported; these derivatives are useful for photoaffinity labeling. Protected or unprotected phenylalanine derivatives were converted to benzoyl derivatives in TfOH at room temperature in a short time without loss of optical purity. The reaction condition was applied to synthesize novel photoreactive phenylalanine derivative, which has two photophores (benzophenone and diazirine). The detail analysis of photo-irradiation for two different photophores contained phenylalanine derivative was also investigated.
  • Lei Wang, Wataru Hisano, Yuta Murai, Munenori Sakurai, Yasuyuki Muto, Haruka Ikemoto, Masashi Okamoto, Takashi Murotani, Reika Isoda, Dongyeop Kim, Yasuko Sakihama, Irnayuli R. Sitepu, Yasuyuki Hashidoko, Yasumaru Hatanaka, Makoto Hashimoto
    MOLECULES 18 (7) 8393 - 8401 1420-3049 2013/07 [Refereed][Not invited]
     
    Photoaffinity labeling is a reliable analytical method for biological functional analysis. Three major photophores-aryl azide, benzophenone and trifluoromethyldiazirine-are utilized in analysis. Photophore-bearing L-phenylalanine derivatives, which are used for biological functional analysis, were inoculated into a Klebsiella sp. isolated from the rhizosphere of a wild dipterocarp sapling in Central Kalimantan, Indonesia, under nitrogen-limiting conditions. The proportions of metabolites were quite distinct for each photophore. These results indicated that photophores affected substrate recognition in rhizobacterial metabolic pathways, and differential photoaffinity labeling could be achieved using different photophore-containing L-phenylalanine derivatives.
  • Yuta Murai, Katsuyoshi Masuda, Yui Ogasawara, Lei Wang, Yasuyuki Hashidoko, Yasumaru Hatanaka, So Iwata, Takuya Kobayashi, Makoto Hashimoto
    European Journal of Organic Chemistry (12) 2428 - 2433 1434-193X 2013/04 [Refereed][Not invited]
     
    2-Phenylethylamine is well known as a substructure of many biologically active compounds, and the synthesis of its photoreactive derivatives to allow the analysis of biological functions is reported. This allowed us to synthesise ligands for adenosine receptors, which have many functional roles in biology and have been extensively studied for their many roles in maintaining homeostasis. Adenosine is one of the most common biochemical compounds, but photoaffinity labeling has not yet been used to study adenosine receptors. Synthetic methods for producing photoreactive adenosine derivatives that can be used with adenosine receptors were established for the photophores phenyl azide and benzophenone. The effect of the introduction of the photoreactive components was determined using an adenosine receptor assay. © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Yuta Murai, Lei Wang, Katsuyoshi Masuda, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, Makoto Hashimoto
    European Journal of Organic Chemistry 2013 (23) 5111 - 5116 1434-193X 2013 [Refereed][Not invited]
     
    Novel hydrogen/deuterium exchange for aromatic α-amino acids and their corresponding peptides were performed through the use of deuterated trifluoromethanesulfonic acid (TfOD). Detailed analysis of the exchange revealed that equal hydrogen/deuterium exchange was observed for phenylalanine, and specific exchange at the ortho-positions of phenol for tyrosine was also detected. The stereochemistry of the aromatic α-amino acids was retained under the exchange conditions. The hydrogen/deuterium exchange properties for these aromatic α-amino acids are identical for peptides that contain several aromatic α-amino acids. The exchange proceeded significantly faster than previous methods. Detailed analysis of the exchange revealed that the method could be controlled by temperature, time, and the amount of reagent. Deuterated trifluoromethanesulfonic acid promotes rapid and controllable hydrogen/deuterium exchange on aromatic rings of α-amino acids and peptides at room temperature and below. The deuterium incorporation depends on the amount of reagent, the temperature, and the time-scale of the reaction. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
  • Yui Ogasawara, Yuta Murai, Yasuko Sakihama, Yasuyuki Hashidoko, Makoto Hashimoto
    HETEROCYCLES 86 (1) 735 - 743 0385-5414 2012/12 [Refereed][Not invited]
     
    The click reaction is one of the latest techniques for the chemical modification of bioactive compounds. Chemical modifications of alpha-amino acid side chains are gaining significance as useful and important tools for biochemical research. Biotinylation at side chain of propargylglycine using click reaction was examined. The detail quantitative analysis of Cu(I) concentration are performed to proceed the click reaction effectively.
  • Quantitative determination of click reaction in the presence of glycine derivatives and in dilute solution
    Yui Ogasawara, Yuta Murai, Yasuko Sakihama, Yasuyuki Hashidoko, Makoto Hashimoto
    International Journal of Organic Chemistry 2 (3) 302 - 304 2012/11 [Refereed][Not invited]
  • Yasuyuki Muto, Yuta Murai, Yasuko Sakihama, Yasuyuki Hashidoko, Makoto Hashimoto
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 76 (11) 2162 - 2164 0916-8451 2012/11 [Refereed][Not invited]
     
    Biotin is one of the most useful tags in (bio)analytical science due to its specific interaction with avidin, but is not easy to convert because of its low solubility in most solvents. Friedel-Crafts acylation of biotin acid chloride in triflic acid was examined, and the synthesized derivatives had stronger affinity to avidin than biotin in a binding assay using 2-(4'-hydroxyphenylazo)benzoic acid.
  • Yuta Murai, Katsuyoshi Masuda, Yasuko Sakihama, Yasuyuki Hashidoko, Yasumaru Hatanaka, Makoto Hashimoto
    JOURNAL OF ORGANIC CHEMISTRY 77 (19) 8581 - 8587 0022-3263 2012/10 [Refereed][Not invited]
     
    5- and 6-trifluoromethyldiazirinyl indoles were synthesized from corresponding bromoindole derivatives for the first time. They acted as mother skeletons for the comprehensive synthesis of various bioactive indole metabolites. These can be used in biological functional analysis as diazirine-based photoaffinity labels.
  • Yuka Tsunekawa, Katsuyoshi Masuda, Miho Muto, Yasuyuki Muto, Yuta Murai, Yasuyuki Hashidoko, Yoshitake Orikasa, Yuji Oda, Yasumaru Hatanaka, Makoto Hashimoto
    HETEROCYCLES 84 (1) 283 - 290 0385-5414 2012/01 [Refereed][Not invited]
     
    As the 1'-hydroxyl group of sucrose is well known to be less reactive than other primary alcohols, there are no reports on the substitution of a phenoxy group at this position. Chemo-enzymatic synthesis of photoreactive 1'-phenoxy-substituted sucrose was examined to elucidate the functional analysis of sweet receptors.
  • Yuta Murai, Yasuyuki Hashidoko, Makoto Hashimoto
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 75 (2) 352 - 354 0916-8451 2011/02 [Refereed][Not invited]
     
    We report here a novel synthesis of optically active bishomotyrosine. The bishomotyrosine skeleton was constructed by using a Friedel-Crafts reaction between phenol and optically active N-Tfa-Glu(Cl)-OMe in triflic acid under the mild condition. Reduction and subsequent deprotection then afforded bishomotyrosine derivatives without any loss of optical purity.
  • Ryo Murashige, Yuka Hayashi, Syo Ohmori, Ayuko Torii, Yoko Aizu, Yasuyuki Muto, Yuta Murai, Yuji Oda, Makoto Hashimoto
    TETRAHEDRON 67 (3) 641 - 649 0040-4020 2011/01 [Refereed][Not invited]
     
    Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form. (C) 2010 Elsevier Ltd. All rights reserved.
  • Yuta Murai, Miho Takahashi, Yasuyuki Muto, Yasumaru Hatanaka, Makoto Hashimoto
    HETEROCYCLES 82 (1) 909 - 915 0385-5414 2010/12 [Refereed][Not invited]
     
    Post-functional deuterium incorporation into diazirinyl acetophenone derivatives is reported. Treatment of the compounds with sodium hydroxide in CH3OD at rt for 10 min achieved deuterium incorporation at alpha-position of the carbonyl group without decomposition of diazirinyl ring. Further deuterium can introduce by reduction of benzyl carbonyl with triethylsilane-d-TFA. Straightforward deuterium introduction into diazirinyl derivatives may contribute to the functional analysis of low molecular compounds with diazirine-based photoaffinity labeling.
  • Ryo Murashige, Yuta Murai, Yasumaru Hatanaka, Makoto Hashimoto
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY 73 (6) 1377 - 1380 0916-8451 2009/06 [Refereed][Not invited]
     
    The Friedel-Crafts reaction with 3-(3-methoxy-phenyl)-3-(trifluoromethyl)-3H-diazirine and optically active N-TFA-Asp(Cl)-OMe in triflic acid afforded homophenylalanine derivatives without any loss of the optical purity.
  • Yuta Murai, Yasumaru Hatanaka, Yulichi Kanaoka, Makoto Hashimoto
    HETEROCYCLES 79 359 - 364 0385-5414 2009/04 [Refereed][Not invited]
     
    Effective incorporation of phenyldiazirine moiety on the acyl residue of (L)- and (D)- glutamic acid by Friedel-Crafts reactions with triflic acid developed simple preparation of bishomophenylalanine (bhPhe) for aromatics, which added a versatile and a reliable access to photoreactive peptide probes.

MISC

Educational Activities

Teaching Experience

  • Laboratory Work on Bio-macromolecular Science II
    開講年度 : 2020
    課程区分 : 学士課程
    開講学部 : 理学部
    キーワード : 物理学実験,化学分析実験,有機合成実験,生化学実験, 分子生物学実験,細胞生物学実験, 生物物理学実験
  • Polymer Synthetic Chemistry
    開講年度 : 2020
    課程区分 : 学士課程
    開講学部 : 理学部
    キーワード : 有機合成、高分子合成、モノマー、ポリマー、ラジカル、芳香族、ベンゼン、カルボニル、重合
  • Bio-Organic Chemistry
    開講年度 : 2020
    課程区分 : 学士課程
    開講学部 : 理学部
    キーワード : アルキン、非局在化電子、付加反応、求核置換反応、脱離反応、ハロゲン化アルキル、有機電子論、アルコール、エーテル、エポキシド、アミン、チオール、有機金属化合物


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