Construction of the standard chiroptical analysis method by vibrational circular dichroism

2010 Fiscal Year Final Research Report

• Project/Area Number: 20310127
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Living organism molecular science
• Research Institution: Hokkaido University
• Principal Investigator: MONDE Kenji Hokkaido University, 大学院・先端生命科学研究院, 教授 (40210207)
• Co-Investigator(Kenkyū-buntansha): MIURA Nobuaki 北海道大学, 大学院・先端生命科学研究院, 特任准教授 (80372267) ; TANIGUCHI Tohru 北海道大学, 大学院・先端生命科学研究院, 助教 (00587123)
• Co-Investigator(Renkei-kenkyūsha): MIURA Nobuaki 北海道大学, 大学院・先端生命科学研究院, 特任准教授 (80372267)
• Project Period (FY): 2008 – 2010
• Keywords: 生体機能関連物質 / トランス脂肪酸

Research Abstract

Glycerolipids are essential substances for sustaining our life. Although the number of their chiral carbon is only one like most of amino acids, their stereochemistry has not been assigned with ease. In order to establish a new analytical method for determination of their absolute configurations, optically pure glycerolipids and related compounds were prepared by chemical synthesis, and subjected to the "Vibrational Circular Dichromism" measurement. The precise analysis of their spectral data resulted in a discovery of an empirical rule on the stereochemistry of diacylglycerolipids including glycolipids for the first time.

Research Products

• [Journal Article] A Vibrational Circular Dichroism Approach to the Determination of the Absolute Configurations of Flavorous 5-Substituted-2(5H)-furanones (2011)
  • Author(s): Nakahashi A., Yaguchi Y., Miura N., Emura M., Monde K.
  • Journal Title: J.Nat.Prod. 74 Pages: 707-711
  • Peer Reviewed
• [Journal Article] Salvileucalin C, a novel rearranged neoclerodane diterpene from Salvia leucantha (2011)
  • Author(s): Aoyagi Y., Yamazaki A., Kato R., Tobe F., Fukaya H., Nishikawa T., Nakahashi A., Miura N., Monde K., Takeya K.
  • Journal Title: Tetrahedron Lett. 52 Pages: 1851-1853
  • Peer Reviewed
• [Journal Article] (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 (2010)
  • Author(s): Kuwahara S., Obata K., Fujita T., Miura N., Nakahashi A., Monde K., Harada N.
  • Journal Title: Eur.J.Org.Chem. Pages: 6385-6392
  • Peer Reviewed
• [Journal Article] (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 (2010)
  • Author(s): Fujita T., Obata K., Kuwahara S., Nakahashi A., Monde K., Decatur J., Harada N.
  • Journal Title: Eur.J.Org.Chem. Pages: 6372-6384
  • Peer Reviewed
• [Journal Article] Super Water- and Highly Oil-Repellent Films Made of Fluorinated Poly(alkylpyrroles) (2010)
  • Author(s): Chiba K., Kurogi K., Monde K., Hashimoto M., Yoshida M., Mayama H., Tsujii K.
  • Journal Title: Colloids Surf., A 354 Pages: 234-239
  • Peer Reviewed
• [Journal Article] Stereochemical Study of a Novel Tautomeric Furanone, Homofuraneol (2009)
  • Author(s): Monde K., Nakahashi A., Miura N., Yaguchi Y., Sugimoto D., Emura M.
  • Journal Title: Chirality 21 Pages: S110-S115
  • Peer Reviewed
• [Journal Article] Stereochemical Studies of Flavorous 2-Substituted-3(2H)-furanones by Vibrational Circular Dichroism (2009)
  • Author(s): Emura M., Yaguchi Y., Nakahashi A., Sugimoto D., Miura N., Monde K.
  • Journal Title: J.Agric.Food Chem. 57 Pages: 9909-9915
  • Peer Reviewed
• [Journal Article] Stereochemical studies of hexylitaconic acid, an inhibitor of p53-HDM2 interaction (2009)
  • Author(s): Nakahashi A., Miura N., Monde K., Tsukamoto S.
  • Journal Title: Bioorg.Med.Chem.Lett. 19 Pages: 3027-3030
  • Peer Reviewed
• [Journal Article] Absolute Configuration of Actinophyllic Acid as Determined through Chiroptical Data (2009)
  • Author(s): Taniguchi T., Martin C., Monde K., Nakanishi K., Berova N., Overman L.
  • Journal Title: J.Nat.Prod. 72 Pages: 430-432
  • Peer Reviewed
• [Journal Article] Vibrational CD Spectroscopy as a Powerful Tool for Stereochemical Study of Cyclophynes in Solution (2009)
  • Author(s): An D.L., Chen Q., Fang J., Yan H., Orita A., Miura N., Nakahashi A., Monde K., Otera J.
  • Journal Title: Tetrahedron Lett. 50 Pages: 1689-1692
  • Peer Reviewed
• [Journal Article] Stereochemical Study of Chiral Tautomeric Flavorous Furanones by Vibrational Circular Dichroism (2008)
  • Author(s): Yaguchi Y., Nakahashi A., Miura N., Sugimoto D., Monde K., Emura M.
  • Journal Title: Org.Lett. 10 Pages: 4883-4885
  • Peer Reviewed
• [Journal Article] Chiral Sulfinates Studied by Optical Rotation, ECD and VCD : the Absolute Configuration of a Cruciferous Phytoalexin Brassicanal C (2008)
  • Author(s): Taniguchi T., Monde K., Nakanishi K., Berova N.
  • Journal Title: Org.Biomol.Chem. 6 Pages: 4399-4405
  • Peer Reviewed
• [Journal Article] Alterations in the glycoform of cisplatin-resistant human carcinoma cells are caused by defects in the endoplasmic reticulum-associated degradation system (2008)
  • Author(s): 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.
  • Journal Title: Cancer Lett. 270 Pages: 295-301
  • Peer Reviewed
• [Presentation] Environment-friendly synthesis of chiral fluorous sphingolipids for metabolic analysis (2010)
  • Author(s): S.Saito, M.Yoshida, A.Nakahashi, M.A.Hammam, S.Mitsutake, Y.Igarashi, K.Monde
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: Hawaii Convention Center Honolulu, Hawaii, USA(Poster)
  • Year and Date: 2010-12-19
• [Presentation] Stereochemical study of sphingolipid derivatives by vibrational circular dichroism (2010)
  • Author(s): A.Nakahashi, M.A.Hammam, S.Saito, K.Monde
  • Organizer: 2010 International Chemical Congress of Pacific Basin Societies (PACIFICHEM 2010)
  • Place of Presentation: Hawaii Convention Center Honolulu, Hawaii, USA(Poster)
  • Year and Date: 2010-12-19
• [Presentation] Vibrational Circular Dichroism (VCD) Studies of Carbohydrates and Glycoconjugates (2010)
  • Author(s): K.Monde, A.Nakahashi, T.Taniguchi, M.Shibata, M.Fukuzawa, N.Miura
  • Organizer: The 25th International Carbohydrate Symposium (ICS2010)
  • Place of Presentation: Makuhari Messe International Convention Complex Tokyo(Chiba), Japan(Oral)
  • Year and Date: 2010-08-02
• [Presentation] VIBRATIONAL CIRCULAR DICHROISM & ITS APPLICATION IN BIOMOLECULAR SCIENCE (2010)
  • Author(s): Kenji Monde, Atsufumi Nakahashi, Masataka Shibata, Tohru Taniguchi, Shota Saito, Mostafa A.S.Hammam, Nobuaki Miura
  • Organizer: 21st International Symposium on Chirality, Chirality 2010
  • Place of Presentation: Sapporo Convention Center, Sapporo, Japan(Oral)
  • Year and Date: 2010-07-15
• [Presentation] ENVIRONMENT-FRIENDLY SYNTHESIS OF CHIRAL FLUOROUS SPHINGOLIPIDS FOR METABOLIC ANALYSIS (2010)
  • Author(s): Shota Saito, Masafumi Yoshida, Atsufumi Nakahashi, Mostafa A.S.Hammam, Tohru Taniguchi, Susumu Mitsutake, Yasuyuki Igarashi, Kenji Monde
  • Organizer: 21st International Symposium on Chirality, Chirality 2010
  • Place of Presentation: Sapporo Convention Center, Sapporo, Japan(Poster)
  • Year and Date: 2010-07-14
• [Presentation] CHIROPTICAL ANALYSIS OF CARBOHYDRATES AND LIPIDS BY VIBRATIONAL CIRCULAR DICHROISM (2010)
  • Author(s): Tohru Taniguchi, Masataka Shibata, Masumi Fukuzawa, Atsufumi Nakahashi, Kenji Monde
  • Organizer: 21st International Symposium on Chirality, Chirality 2010
  • Place of Presentation: Sapporo Convention Center, Sapporo, Japan(Poster)
  • Year and Date: 2010-07-13
• [Presentation] CHIROPTICALANALYSIS OF CARBOHYDRATES AND LIPIDS USING VIBRATIONAL CIRCULAR DICHROISM (2010)
  • Author(s): Kenji Monde
  • Organizer: ICOPVS 2010-The 3rd International Conference on Perspectives in Vibrational Spectroscopy
  • Place of Presentation: Dept.of Physics, Banaras Hindu University, Varanasi, India(Invited)
  • Year and Date: 2010-02-22
• [Presentation] Stereochemical studies of hexylitaconic acid, an inhibitor of p53-HDM2 interaction (2009)
  • Author(s): Nakahashi A., Miura N., Monde K., Tsukamoto S.
  • Organizer: 21st International Symposium on Chirality, Chirality 2009
  • Place of Presentation: Breckenridge, Colorado, USA(Poster)
  • Year and Date: 20090713-20090714
• [Presentation] Stereochemical Study of Chiral Tautomeric Flavorous Furanones by Vibrational Circular Dichroism (2009)
  • Author(s): Nakahashi A., Miura N., Monde K., Emura M., Yaguchi Y., Sugimoto D.
  • Organizer: 21st International Symposium on Chirality, Chirality 2009
  • Place of Presentation: Breckenridge, Colorado, USA(Poster)
  • Year and Date: 20090713-20090714
• [Presentation] Chiroptical Analysis of Glycoconjugates by Vibrational Circular Dichroism (2009)
  • Author(s): Nakahashi A., Taniguchi T., Fukuzawa M., Nishimura S.-I., Monde K.
  • Organizer: International Joint Symposium of "The 6thSymposium for Future Drug Discovery and Medical Care" and "Symposium of the Research Center for Cooperative Projects"
  • Place of Presentation: Sapporo, Japan
  • Year and Date: 20090313-20090314
• [Presentation] Vibrational circular dichroism-Powerful tool for stereochemical analysis of biomolecules- (2009)
  • Author(s): Kenji Monde, Masataka Shibata, Atsufumi Nakahashi, Masumi Fukuzawa, Mai Hashimoto, Tohru Taniguchi, Nobuaki Miura
  • Organizer: International Conference on Current Trends in Chemistry and Biochemistry
  • Place of Presentation: Bangalore University, Bangalore, India
  • Year and Date: 2009-12-18
• [Presentation] Chirality of Lipids (2009)
  • Author(s): Monde K.; Shibata M.; Nakahashi A.; Fukuzawa M.; Taniguchi T.; Miura N.
  • Organizer: CD 2009-12th International Conference on Circular Dichroism, ISBC-5th Interdisciplinary Symposium on Biological Chirality
  • Place of Presentation: University of Brescia, Italy(Oral)
  • Year and Date: 2009-09-03
• [Presentation] Chiroptical Analysis of Lipids & Glycolipids by Vibrational Circular Dichroism (2009)
  • Author(s): Monde K.; Shibata M.; Nakahashi A.; Fukuzawa M.; Taniguchi T.; Miura N.; Nishimura S.I.
  • Organizer: 21st International Symposium on Chirality, Chirality 2009
  • Place of Presentation: Breckenridge, Colorado, USA(Oral)
  • Year and Date: 2009-07-13
• [Presentation] What can we do for Biomolecules using Vibrational Circular Dichroism (VCD)?-Chiroptical Analysis of Glycoconjugates and Related Materials-. (2008)
  • Author(s): Monde K.
  • Organizer: CRC International Symposium on Bio-interface and Conversion
  • Place of Presentation: Sapporo, JAPAN
  • Year and Date: 20081000
• [Presentation] Vibrational circular dichroism study on lipids & glycolipids. (2008)
  • Author(s): Monde K., Shibata M., Fukuzawa M., Nakahashi A., Taniguchi T., Miura N.
  • Organizer: 20th International symposium on chirality (ISCD-20)
  • Place of Presentation: Geneva, Switzerland
  • Year and Date: 20080706-20080709
• [Presentation] ABSOLUTE STEREOCHEMISTRY OF FLAVOR RELATED 2-SUBSTITUTED-3(2H)-FURANONES, 2,5-DIMETHYL-4-HYDROXY-3(2H)-FU RANONE AND ANALOGUES (2008)
  • Author(s): Makoto Emura, YOSHIHIRO YAGUCHI, Daisuke Sugimoto, Atsufumi Nakahashi, Nobuaki Miura, Kenji Monde
  • Organizer: The 12th International Weurman Flavour Research Symposium
  • Place of Presentation: Interlaken, Swiss(Poster)
  • Year and Date: 20080701-20080704
• [Presentation] Theoretical Calculation of Optical Activity (2008)
  • Author(s): Taniguchi Tohru ; Monde Kenji ; Gerhard Schlingmann ; Nakanishi Koji ; Berova Nina
  • Organizer: Absolute Configurations of Phytoalexins and Other Natural Products.(50th 281-284)
  • Place of Presentation: Tennen Yuki Kagobutsu Toronkai Koen Yoshishu
  • Year and Date: 20080000
• [Book] Comprehensive Chiroptical Spectroscopy(Ed.Nina Berova, Prasad Polavarapu, Koji Nakanishi, Robert Woody)(Electronic Circular Dichroism and Vibrational Circular Dichroism of Glycoconjugates) (2011)
  • Author(s): Taniguchi T., Monde K.
  • Publisher: JohnWiley & Sons(in press.)