化学生物学研究室
Laboratory of Molecular Chemical Biology (Monde Lab.)
Hokkaido University, Faculty of Advanced Life Science
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    Prof. Monde
   
Publication
 
 2022
  Santanu Mondal, Ravindra D. Aher, Venkati Bethi, Yu-Ju Lin, Tohru Taniguchi, Kenji Monde, Fujie Tanaka
Control of Reactions of Pyruvates by Catalysts: Direct Enantioselective Mannich Reactions of Pyruvates Catalyzed by Amine-based Catalyst Systems
Org. Lett., 24, 1853-1858 (2022)

Yuta Murai, Kohei Yuyama, Daisuke Mikami, Yasuyuki Igarashi, Kenji Monde
Penta-deuterium-labeled 4E, 8Z-sphingadienine for rapid analysis in sphingolipidomics study
Chem. Phys. Lipids, 245, 105202 (2022)

Yuta Murai, Akihiro Sekiguchi, Taeko Hirakawa, Seigo Usukia, Yasuyuki Igarashi, Kenji Monde
Evaluation of Chiral N,N-Dimethyl-Sphingosine for the interaction between NGF and trkA
Chirality, 34, 807-812 (2022)

Mohamad Zarif Mohd Zubir, Nurul Fajry Maulida, Yoshihiro Abe, Yuta Nakamura, Mariam Abdelrasoul, Tohru Taniguchi, Kenji Monde
Deuterium labelling to extract local stereochemical information by VCD spectroscopy in the C-D stretching region: a case study of sugars
Org. Biomol. Chem., 20, 1067-1072 (2022)

 2021
  Tohru Taniguchi, Mohamad Zarif Mohd Zubir, Nobuyuki Harada, Kenji Monde
Exploration of chromophores for a VCD couplet in a spectrally transparent infrared region for biomolecules
Phys. Chem. Chem. Phys., 23, 27525-27532 (2021).

Nariyoshi Umekubo, Tohru Taniguchi, Kenji Monde, Yujiro Hayashi Synthesis of Bicyclo[2.2.2]octanes with a Quaternary Bridgehead Carbon by Diphenylprolinol Silyl Ether-mediated Domino Reaction
Asian J. Org. Chem., 10 (12), 3261-3265 (2021)

Seitaro Koshino, Tohru Taniguchi, Kenji Monde, Eunsang Kwon, Yujiro Hayashi
Enantiodivergent One-Pot Synthesis of Axially Chiral Biaryls Using Organocatalyst-Mediated Enantioselective Domino Reaction and Central-to-Axial Chirality Conversion
Chem. Eur. J., 27, 15786-15794 (2021).

Mahadeva M. M. Swamy, Yuta Murai, Kenji Monde, Setsuko Tsuboi, and Takashi Jin
Shortwave-Infrared Fluorescent Molecular Imaging Probes Based on π-Conjugation Extended Indocyanine Green
Bioconjugate Chem.,32 (8), 1541-1547 (2021)

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
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-
薬理と治療 49(8), 1225-1239 (2021)

 2020
  門出健次
前田耕治、安川智之、床波志保 編 
機器分析ハンドブック2 ー高分子・分析技術編ー10章 140-153(2020)
旋光度と円偏光二色法(CD) 化学同人

門出健次、日本化学会 編 化学便覧 基礎編 改訂6版15章 97-98 (2020)
分光学的性質 ―生体物質の円二色性― 丸善出版㈱

門出 健次,村井 勇太
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
生化学, 92 (2), 272-277(2020)

Hadya Virupaksha Deepak, Mahadeva M. M. Swamy, Yuta Murai, Yoshiko Suga, Masaki Anetai, Takuro Yo, Masahiro Kuragano, Koji Uwai, Kiyotaka Tokuraku and Kenji Monde
Daurichromenic Acid from the Chinese Traditional Medicinal Plant Rhododendron dauricum Inhibits Sphingomyelin Synthase and Aβ Aggregation
Molecules, 25, 4077-4088 (2020)

Usuki S., Yasutake Y., Tamura N., Tamura T., Tanji K., Saitoh T., Murai Y., Mikami D., Yuyama K., Monde K., Mukai K., Igarashi Y.
Nrp1 is activated by kCer binding-induced structural rigidification of the a1a2 domain
Cells, 9, 517-535 (2020)

Koshino S., Takikawa A., Ishida K., Taniguchi T., Monde K., Kwon E., Umemiya S., Hayashi Y.
Inversion of the axial information during oxidative aromatization in the synthesis of axially chiral biaryls using organocatalyst as a key step
Chem. Eur. J., 26, 4524-4530 (2020)

Lkhamkhuu E., Zikihara K., Katsura H., Tokutomi S., Hosokawa T., Usami Y., Ichihashi M., Yamaguchi J., Monde K.
Effect of Circularly Polarized Light on Germination, Hypocotyl Elongation and Biomass Production of Arabidopsis and Lettuce; Involvement of Phytochrome B
Plant Biotechnology, 37, 57-67 (2020)

Koolath S., Murai, Y., Suga, Y., Monde, K.
Chiral Combinatorial Preparation and Biological Evaluation of Unique Ceramides for Inhibition of Sphingomyelin Synthase
Chirality, 32, 308-313 (2020)

 2019
  Saaidin S. A., Murai, Y., Ishikawa, T., Monde, K.
Design and Synthesis of Ligand‐Tag Exchangeable Photoaffinity Probe Utilizing Nosyl Chemistry
Eur. J. Org. Chem., 2019, 7563-7567 (2019)

Okamura, H., Fujioka, T., Mori, N., Taniguchi, T., Monde, K., Watanabe, H., Takikawa, H.
First enantioselective synthesis of salinipostin A, a marine cyclic enol-phosphotriester isolated from Salinispora sp
Tetrahedron Lett., 60, 150917-150919 (2019)

Othman, M. A., Yuyama, K., Murai, Y., Igarashi, Y., Mikami, D., Sivasothy, Y., Awang, K., Monde, K.
Malabaricone C as Natural Sphingomyelin Synthase Inhibitor against Diet-Induced Obesity and Its Lipid Metabolism in Mice
ACS Med. Chem. Lett., 10, 1154-1158 (2019)

村井勇太、門出健次
セラミド研究会 編 セラミド研究の新展開 ~基礎から応用へ~
第33章 278-285(2019)”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

Sasaki, R., Tainaka, R., Ando, Y., Hashi, Y., Virupaksha, D., Suga, Y., Murai, Y., Anetai, M., Monde, K., Ota, K., Ito, I., Kikuchi, H., Oshima, Y., Endo, Y., Nakao, H., Sakono, M., Uwai, K., Tokuraku K.
An automated microliter-scale high-throughput screening system (MSHTS) for real-time monitoring of protein aggregation using quantum-dot nanoprobes
Sci. Rep., 9, 2587 (2019)

Kiske, C., Riegel, A., Hopf, R., Kvindt, A., Poplacean, I., Taniguchi, T., Swamy, M., Monde, K., Eisenreich, W., Engel, K.
Determination of the Absolute Configurations and the Sensory Properties of the Enantiomers of a Homologous Series (C6?C10) of 2-Mercapto-4-alkanones
J. Agric. Food Chem., 67, 1187-1196 (2019)

2018
  Taniguchi, T., Nakano, K., Monde, K.
Stereochemistry (and Conformation) of Nucleosides and Their Synthetic Precursors by Vibrational Circular Dichroism
Current Protocols in Nucleic Acid Chemistry, 72, 7.29.1-7.29.9 (2018)

Taniguchi, T., Suzuki, T., Satoh, H., Shichibu, Y., Konishi, K., Monde, K.
Preparation of Carbodiimides with One-Handed Axial Chirality
J. Am. Chem. Soc., 140, 15577-15581 (2018)

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

Swamy, M. M. M., Murai, Y., Ohno, Y., Jojima, K., Kihara, A., Mitsutake, S., Igarashi, Y., Yu, J., Yao, M., Suga, Y., Anetai, M., Monde, K.
Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor
Chem. Commun., 54, 12758-12761 (2018)

Murakami R., Sano K., Iwai T., Taniguchi T., Monde K., Sawamura M.
Palladium-Catalyzed Asymmetric C(sp3)-H Allylation of 2-Alkylpyridines
Angew. Chem., Int. Ed., 57, 9465-9469 (2018)

Kawauchi G., Umemiya S., Taniguchi T., Monde K., Hayashi Y.
Enantio- and Diastereoselective Synthesis of Latanoprost using an Organocatalyst
Chem. Eur. J., 24, 8409-8414 (2018)

Gowda S. B., Nakahashi A., Yamane, K., Nakahashi, S., Murai, Y., C. Siddegowda, A. K., Hammam M. A. S., Monde, K.
Facile Chemoselective Strategy toward Capturing Sphingoid Bases by Unique Glutaraldehyde Functionalized Resin
ACS Omega, 3, 753-759 (2018)

Hongen, T., Taniguchi, T., Monde, K.
Modifying oligoalanine conformation by replacement of amide to ester linkage
Chirality, 30, 396–401 (2018)

2017
  Narita, K., Sato, H., Minami, A., Kudo, K., Gao, L., Liu, C., Ozaki, T., Kodama, M., Lei, X., Taniguchi, T., Monde, K., Yamazaki, M., Uchiyama, M., Oikawa, H.
Focused genome mining of structurally related sesterterpenes: enzymatic formation of enantiomeric and diastereomeric products
Org. Lett., 19, 6696-6699(2017)

門出健次、村井勇太
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
化学, 72 (10), 70-71 (2017)

Reyes R. L., Harada T., Taniguchi T., Monde K., Iwai T., Sawamura M.
Enantioselective Rh- or Ir-Catalyzed Directed C(sp3)–H Borylation with Phosphoramidite Chiral Ligands
Chem. Lett., 46, 1747-1750 (2017)

Takayama Y., Ishii T., Ohmiya H., Iwai T., Schwarzer M. C., Mori S., Taniguchi T., Monde K., Sawamura M.
Asymmetric Synthesis of β-Lactams through Copper-Catalyzed Alkyne-Nitrone Coupling with Prolinol-Phosphine Chiral Ligand
Chem., Eur. J., 23, 8400-8404 (2017)

谷口透、門出健次
円二色性(CD)・赤外円二色性(VCD)による立体構造解析 ~実践例と注意点~
有機合成化学協会誌 75, 522-529 (2017)

Huang, J.-R., Sohail, M., Taniguchi, T., Monde, K., Fujie Tanaka, F.
Formal (4+1) Cycloaddition and Enantioselective Michael?Henry Cascade Reactions To Synthesize Spiro[4,5]decanes and Spirooxindole Polycycles
Angew. Chem., Int. Ed., 56, 5853-5857 (2017)

Taniguchi, T., Nakano, K., Baba, R., Monde, K.
Analysis of Configuration and Conformation of Furanose Ring in Carbohydrate and Nucleoside by Vibrational Circular Dichroism
Org. Lett., 19, 404-407 (2017)

Kasamatsu, K., Yoshimura, T., Mandi, A., Taniguchi, T., Monde, K., Furuta, T., Kawabata, T.
α-Arylation of α-Amino Acid Derivatives with Arynes via Memory of Chirality: Asymmetric Synthesis of Benzocy-clobutenones with Tetrasubstituted Carbon
Org. Lett., 19, 352-355 (2017)

Saito, S., Murai,Y., Usuki, S., Yoshida, M., Hammam, M.A.S., Mitsutake, S., Yuyama, K., Igarashi, Y., Monde, K.
Synthesis of Nontoxic Fluorous Sphingolipids as Molecular Probes of Exogenous Metabolic Studies for Rapid Enrichment by FSPE
Eur. J. Org. Chem., 2017, 1045-1051 (2017)

2016
  Kiske, C., Noerenberg, S., Ecker, M., Ma, X., Taniguchi, T., Monde, K., Eisenreich, W., Engel, K.-H.
Reinvestigation of the Absolute Configurations of Chiral s-Mercaptoalkanones Using Vibrational Circular Dichroism and 1H NMR Analysis
J. Agric. Food Chem., 64, 8563-8571 (2016)

Hayashi, Y., Bondzic, B. P., Yamazaki, T., Gupta, Y., Ogasawara, S., Taniguchi, T., Monde, K.
Asymmetric Diels–Alder Reaction of α-Substituted and β,β-Disubstituted α,β-Enals via Diarylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereocenters
Chem., Eur. J., 22, 15874-15880 (2016)

門出健次、谷口透
VCD励起子キラリティー法
分光研究, 65, 137-144 (2016)

Taniguchi, T., Hongen, T., .Monde, K.
Studying the stereostructures of biomolecules and their analogs by vibrational circular dichroism.
Polym. J. 48, 925–931 (2016)

Mizutani, S., Komori, K., Taniguchi, T., Monde, K., Kuramochi, K., Tsubak, K.
A Bioinspired Synthesis of (±)-Rubrobramide, (±)-Flavipucine, and Isoflavipucine
Angew. Chem., Int. Ed., 55, 9553-9556 (2016)

Nakahashi, A., C. Siddegowda, A. K., Hammam, M. A. S., Gowda, S. G. B., Murai, Y., Monde, K.
Stereochemical study of sphingosine by vibrational circular dichroism
Org. Lett., 18, 2327-2330 (2016)

Taniguchi T., Asahata M., Nasu A., Shichibu Y., Konishi K., Monde K.
Facile Diastereoseparation of Glycosyl Sulfoxides by Chiral Stationary Phase
Chirality, 28, 534-539 (2016)

Mandi A., Swamy M. M. M., Taniguchi T., Anetai M., Monde K.
Reducing Molecular Flexibility by Cyclization for Elucidation of Absolute Configuration by CD Calculations: Daurichromenic Acid
Chirality, 28, 453-459 (2016)

Wang, S., Taniguchi, T., Monde, K., Kawahata, M., Yamaguchi, K., Otani, Y., Ohwada T.
Hydrogen Bonding to Carbonyl Oxygen of Nitrogen-Pyramidalized Amide – Detection of Pyramidalization Direction Preference by Vibrational Circular Dichroism Spectroscopy
Chem. Commun., 52, 4018-4021 (2016)

Kato, M., Hammam, M. A. S., Taniguchi, T., Suga, Y., Monde, K.
What Is the True Structure of D609, a Widely Used Lipid Related Enzyme Inhibitor?
Org. Lett., 18, 768-771 (2016)

Tahara, Y., Obinata, S., Kanyiva, K. S., Shibata, T., Mándi, A., Taniguchi, T., Monde, K.
Enantioselective Synthesis of Aminoindan Carboxylic Acid Derivatives by the Catalytic Intramolecular [2+2+2] Cycloaddition of Amino Acid-Tethered Triynes
Eur. J. Org. Chem., 2016, 1405-1413, (2016)

Swamy M. M. M., Mandi A., Anetai M., Monde K.
Stereochemistry of a Rhododaurichromanic Acid Derivative.
Nat. Prod. Commun., 11, 193-195 (2016)

Asai, T., Morita, S., Taniguchi, T., Monde, K., Oshima, Y.
Epigenetic stimulation of polyketide production in Chaetomium cancroideum by an NAD+- dependent HDAC inhibitor.
Org. Biomol. Chem., 14, 646-651 (2016)

Gowda S.B., Usuki S., Hammam M.A.S., Murai Y., Igarashi Y., Monde K.,
Highly Efficient Preparation of Sphingoid Bases from Glucosylceramides by Chemoenzymatic Method,
J. Lipid Res.,
57,
325-331 (2016)

2015
  Yaguchi, Y., Nakahashi, A., Miura, N., Taniguchi, T., Sugimoto, D., Emura, M., Zaizen, K., Kusano, Y., .Monde, K.
Vibrational CD (VCD) Spectroscopy as a Powerful Tool for Chiral Analysis of Flavor Compounds.
ACS Symp. Ser., 1212, 35-56 (2015)

Taniguchi, T., Manai, D., Shibata, M., Itabashi, Y., Monde, K.
Stereochemical Analysis of Glycerophospholipids by Vibrational Circular Dichroism.
J. Am. Chem. Soc., 137, 12191–12194 (2015)

Ye, Y., Minami, A., Mandi, A., Liu, C., Taniguchi, T., Kuzuyama, T., Monde, K., Gomi, K., Oikawa H.,
Genome Mining for Sesterterpenes Using Bifunctional Terpene Synthases Reveals a Unified Intermediate of Di/Sesterterpenes.
J. Am. Chem. Soc.,137, 11846–11853 (2015)

Hayashi, Y., Yamazaki, T., Nakanishi, Y., Ono, T., Taniguchi,T., Monde, K., Uchimaru,T.
Asymmetric Nitrocyclopropanation of α-Substituted α,β-Enals Catalyzed by Diphenylprolinol Silyl Ether for the Construction of All-Carbon Quaternary Stereogenic Centers.
Eur.J. Org. Chem., 2015, 5747-5754 (2015)

2014
  Khandelwal, P., Singh, P., Taniguchi, T., Monde, K., Johmoto, K., Uekusa, H., Masubuti, H., Fujimoto, Y.
Revision of the relative and absolute stereochemistry of 3-hydroxydehydroiso-α-lapachone and its derivatives.
Phytochemistry Lett.,
10
, 224-229 (2014)

Salayová, A., Kudličková Z., Baláž M., Budovská M., Pilátová M., Mojžiš J., Monde K., Petrovaj J., Gondová T.
Stereoselective synthesis of 1-methoxyspiroindoline phytoalexins and their amino analogues
Tetrahedron Asymmetry,
25
, 1221-1233 (2014)

Hongen, T., Taniguchi, T. Nomura, S., Kadokawa, J., Monde, K.
In Depth Study on Solution-State Structure of Poly(lactic acid) by Vibrational Circular Dichroism
Macromolecules,
47
, 5313-5319 (2014)

Shibuta, T., Sato, S., Shibuya, M., Kanoh, N., Taniguchi, T., Monde, K., Iwabuchi, Y.
Enantioselective intramolecular aza-spiroannulation onto benzofurans using chiral rhodium catalysis
Heterocycles,
89
, 631-639(2014)

Komori K., Taniguchi T., Mizutani S., Monde K., Kuramochi K., Tsubaki K.i
Short Synthesis of Berkeleyamide D and Determination of the Absolute Configuration by the Vibrational Circular Dichroism Exciton Chirality Method
Org. Lett.
16
, 1386-1389 (2014)

2013
  Asai T., Taniguchi T., Yamamoto T., Monde K., Oshima Y.
Structures of Spiroindicumides A and B, Unprecedented Carbon Skeletal Spirolactones, and Determination of the Absolute Configuration by Vibrational Circular Dichroism Exciton Approach
Org. Lett. 15, 4320-4323 (2013)

Asai, T., Yamamoto T., Shirata N., Taniguchi T., Monde K., Fujii I., Gomi K., Oshima Y.,
Structurally diverse chaetophenol productions induced by chemically mediated epigenetic manipulation of fungal gene expression
Org. Lett. 15, 3346-3349 (2013)

Asai T., Otsuki S., Taniguchi T., Monde K., Yamashita K., Sakurai H., Ozeki T., Oshima Y.
Structures and absolute configurations of short-branched fatty acid dimers from an endophytic fungus of Aloe arborescens
Tetrahedron Lett. 54, 3402-3405 (2013)


2012
  Asai T., Morita S., Shirata N., Taniguchi T., Monde K., Sakurai H., Ozeki T., Oshima Y.
Structural Diversity of New C13-Polyketides Produced by Chaetomium mollipilium Cultivated in the Presence of a NAD+-Dependent Histone Deacetylase Inhibitor
Org. Lett. 14, 5456–5459 (2012)

Taniguchi, T., Monde, K.
The Exciton Chirality Method in Vibrational Circular Dichroism
J. Am. Chem. Soc., 134, 3695–3698 (2012)

Asai, T., Luo, D., Obara, Y., Taniguchi, T., Monde, K., Yamashita, K., Oshima, Y.
Dihydrobenzofurans as cannabinoid receptor ligands from Cordyceps annullata, an entomopathogenic fungus cultivated in the presence of an HDAC inhibitor.
Tetrahedron Lett., 53, 2239-2243 (2012)

Shibata, T., Miyoshi, M., Uchiyama, T., Endo, K., Miura, N., Monde, K.
Enantioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition
Tetrahedron, 68, 2679–2686 (2012)


   
門出健次(理学博士)
北海道大学大学院
先端生命科学研究院 教授

Kenji Monde, Ph. D.
Hokkaido University Faculty of Advanced Life Science, Professor


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