Laboratory of Chemical Biology (Monde Lab.)
Hokkaido University, Faculty of Advanced Life Science
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    Prof. Monde
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., (2017) in press.

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)
  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)

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.,
325-331 (2016)

  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)

  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.,
, 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,
, 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
, 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
, 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.
, 1386-1389 (2014)
  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)
  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)
  Nakahashi, A., Yaguchi, Y., Miura, N., Emura, M., Monde, K.
A Vibrational Circular Dichroism Approach to the Determination of the Absolute Configurations of Flavorous 5-Substituted-2(5H)-furanones
J. Nat. Prod., 74, 707-711 (2011)

Aoyagi, Y., Yamazaki, A., Kato, R., Tobe, F., Fukaya, H., Nishikawa, T., Nakahashi, A., Miura, N., Monde, K., Takeya, K.
Salvileucalin C, a novel rearranged neoclerodane diterpene from Salvia leucantha
Tetrahedron Lett., 52, 1851-1853 (2011)

Taniguchi, T., Monde, K.
Electronic Circular Dichroism and Vibrational Circular Dichroism of Glycoconjugates,
Ed. Nina Berova, Prasad Polavarapu, Koji Nakanishi, Robert Woody,
Comprehensive Chiroptical Spectroscopy,
John Wiley & Sons, in press. (2011)
  Kuwahara, S., Obata, K., Fujita, T., Miura, N., Nakahashi, A., Monde, K., Harada, N.
(R)-(+)-[VCD(-)984]-4-Ethyl-4-methyloctane, a Cryptochiral Hydrocarbon with a Quaternary Chirality Center. (2) Vibrational CD Spectra of Both Enantiomers and Absolute Configurational Assignment
Eur. J. Org. Chem. 6385-6392 (2010)

Fujita, T., Obata, K., Kuwahara, S., Nakahashi, A., Monde, K., Decatur, J., Harada, N.
(R)-(+)-[VCD(-)984]-4-Ethyl-4-methyloctane, a Cryptochiral Hydrocarbon with a Quaternary Chirality Center. (1) Synthesis of Enantiopure Compound and Unambiguous Determination of Absolute Configuration
Eur. J. Org. Chem. 6372-6384 (2010)

Monde, K., Nakahashi, A., Miura, N., Yaguchi, Y., Sugimoto, D., Emura, M.
Stereochemical Study of a Novel Tautomeric Furanone, Homofuraneol
Chirality, 21, S110-S115 (2009).

Chiba, K., Kurogi, K., Monde, K., Hashimoto, M., Yoshida, M., Mayama, H., Tsujii, K.
Super Water- and Highly Oil-Repellent Films Made of Fluorinated Poly(alkylpyrroles)
Colloids Surf., A, 354, 234-239 (2010).
  Emura, M., Yaguchi, Y., Nakahashi, A., Sugimoto, D., Miura, N., Monde, K.
Stereochemical Studies of Flavorous 2-Substituted-3(2H)-furanones by Vibrational Circular Dichroism
J. Agric. Food Chem., 57, 9909-9915. (2009).

Nakahashi, A., Miura, N., Monde, K., Tsukamoto, S.
Stereochemical studies of hexylitaconic acid, an inhibitor of p53-HDM2 interaction
Bioorg. Med. Chem. Lett., 19, 3027–3030 (2009).

Taniguchi, T., Martin, C., Monde, K., Nakanishi, K., Berova, N., Overman, L.
Absolute Configuration of Actinophyllic Acid as Determined through Chiroptical Data
J. Nat. Prod., 72, 430-432 (2009).

An, D. L., Chen, Q., Fang, J., Yan, H., Orita, A., Miura, N., Nakahashi, A., Monde, K., Otera, J.
Vibrational CD Spectroscopy as a Powerful Tool for Stereochemical Study of Cyclophynes in Solution
Tetrahedron Lett.,
50, 1689-1692 (2009).
  Yaguchi, Y., Nakahashi, A., Miura, N., Sugimoto, D., Monde, K., Emura, M.
Stereochemical Study of Chiral Tautomeric Flavorous Furanones by Vibrational Circular Dichroism
Org. Lett. 10, 4883-4885 (2008).

Taniguchi, T., Monde, K., Nakanishi, K., Berova, N.
Chiral Sulfinates Studied by Optical Rotation, ECD and VCD: the Absolute Configuration of a Cruciferous Phytoalexin Brassicanal C
Org. Biomol. Chem., 6, 4399-4405 (2008).

Nakagawa, H., Ohira, M., Hayashi, S., Abe, S., Saito, S., Nagahori, N., Monde, K., Shinohara, Y., Fujitani, N., Kondo, H., Akiyama, S.-I., Nakagawara, A., Nishimura, S.-I.
Alterations in the glycoform of cisplatin-resistant human carcinoma cells are caused by defects in the endoplasmic reticulum-associated degradation system
Cancer Lett., 270, 295-301 (2008).

Nakahara, T., Hashimoto, R., Nakagawa, H., Monde, K., Miura, N., Nishimura, S.-I.
Glycoconjugate Data Bank: Structures---an annotated glycan structure database and N-glycan primary structure verification service
Nucleic Acids Res., 36, D368-D371 (2008).

Taniguchi, T., Tone, I., Monde, K.
Observation and Characterization of a Specific Vibrational Circular Dichroism (VCD) Band in Phenyl Glycosides
Chirality, 20, 446-453 (2008).
  Nakahashi, A., Taniguchi, T. Miura, N., Monde, K.
Stereochemical Studies of Sialic Acid Derivatives by Vibrational Circular Dichroism
Org. Lett., 9, 4741-4744 (2007).

Curillov, Z., Kutschy, P., Budovsk, M., Nakahashi, A., Monde, K.
Stereoselective synthesis of (R)-(+)-1-methoxyspirobrassinin, (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether and their enantiomers, or diastereoisomers
Tetrahedron Lett., 48, 8200-8204 (2007).

Taniguchi, T., Monde, K.
Spectra - Structures Relationship on Carbohydrate VCD and Its Application to Glycoconjugates
Chem.-Asian J., 2, 1258-1266 (2007).

Min, H.M., Aye, M., Taniguchi, T., Miura, N., Monde, K., Ohzawa, K., Nikai, T., Niwa, M., Takaya, Y.
A structure and an absolute configuration of (+)-alternamin, a new coumarin from Murraya alternans having antidote activity against snake venom
Tetrahedron Lett., 48, 6155-6158 (2007).

Sato, H., Taniguchi, T., Nakahashi, A., Monde, K., Yamagishi, A.
Effects of Central Metals Ions on Vibrational Circular Dichroism Spectra of
Tris-(β-diketonato)Metal(III) Complexes
Inorg. Chem., 46, 6755-6766 (2007).

Fujita,T., Obata, K., Kuwahara, S., Miura, N., Nakahashi, A., Monde, K., Decatur, J., Harada, N.
(R)-(+)-[VCD(+)945]-4-Ethyl-4-methyloctane, the Simplest Chiral Saturated Hydrocarbon with a Quaternary Stereogenic Center
Tetrahedron Lett., 48, 4219–4222 (2007).

Taniguchi, T., Monde, K.
Vibrational circular dichroism (VCD) studies on disaccharides in the CH region: Toward discrimination of glycosidic linkage position
Org. Biomol. Chem., 5, 1104–1110 (2007).

Yamane, S., Iwasaki, N., Kasahara, Y., Harada, K. Majima T., Monde, K., Nishmura, S.-I., Minami, A.
The effect of pore size on in vitro cartilage formation using chitosan-based hyaluronic acid hybrid polymer fibers
J. Biomed. Mater. Res., Part A, 81A, 586 - 593 (2007).

高分子学会 編集 高分子分析技術最前線
第Ⅲ部 分子構造の解析 第4章 赤外円二色性スペクトル
165-176 (2007) 共立出版

化学と生物, 45, 455-458 (2007)

Taniguchi, T., Monde, K.,
Chiroptical Analysis of Glycoconjugates by Vibrational Circular Dichroism (VCD)
Trends Glycosci. Glycotech., 19, 149-166 (2007).
  Taniguchi, T., Sato, H., Monde, K., Nishimura, S.-I., Yoshida, J., Yamagishi, A.
Rewinding of Helical Systems by Use of Cr(III) Complex as a Photoresponsive Chiral Dopant
Mol. Cryst. Liq. Cryst., 460, 107-116 (2006).

Monde, K., Taniguchi, T., Miura, N., Vairappan, C. S., Suzuki, M.
Absolute configurations of endoperoxides determined by vibrational circular dichroism (VCD)
Tetrahedron Lett., 47, 4389-4392 (2006).

Monde, K., Miura, N., Hashimoto, M., Taniguchi, T., Inabe, T.
Conformational Analysis of Chiral Helical Perfluoroalkyl Chains by VCD
J. Am. Chem. Soc., 128, 6000-6001 (2006).

Sato, H., Taniguchi, T., Monde, K., Nishimura, S. -I., Yamagishi, A.
Dramatic Effects of d-Electron Configurations on Vibrational Circular Dichroism Spectra of Tris(acetylacetonato)metal (III)
Chem. Lett., 35, 364-365 (2006).

Monde, K., Taniguchi, T., Miura, N., Vairappan, C. S., Suzuki, M.
Absolute Configurations of Brominated Sesquiterpenes Determined by Vibrational Circular Dichroism
Chirality, 18, 335-339 (2006).

Miura, N., Taniguchi, T., Monde, K., Nishimura, S.-I.
A theoretical study of α- and β-D-glucopyranose conformations by the density functional theory
Chem. Phys. Lett., 419, 326-332 (2006).

高分子, 45, 516-519 (2006).
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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