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Practical Configuration Analysis for Natural Products.

Research Project

Project/Area Number 10554043
Research Category

Grant-in-Aid for Scientific Research (B).

Allocation TypeSingle-year Grants
Section展開研究
Research Field 分離・精製・検出法
Research InstitutionOsaka University (1999-2000)
The University of Tokyo (1998)

Principal Investigator

MURATA Michio  Graduate School Science, Osaka University, Professor, 大学院・理学研究科, 教授 (40183652)

Co-Investigator(Kenkyū-buntansha) UTSUMI Hiroaki  Researcher, JEOL Co.LTD., 研究員
TACHIBANA Kazuo  School of Science, The University of Tokyo, Professor, 大学院・理学系研究科, 教授 (70142081)
MATSUMORI Nobuaki  Graduate School of Science, Osaka University, Research Associate, 大学院・理学研究科, 助手 (50314357)
Project Period (FY) 1998 – 2000
Project Status Completed (Fiscal Year 2000)
Budget Amount *help
¥12,900,000 (Direct Cost: ¥12,900,000)
Fiscal Year 2000: ¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 1999: ¥4,400,000 (Direct Cost: ¥4,400,000)
Fiscal Year 1998: ¥6,000,000 (Direct Cost: ¥6,000,000)
KeywordsNMR / spin coupling constants / J values / configuration / conformation / natural products / maitotoxin / amphidinol / 鎖状構造
Research Abstract

A method for elucidating the relative configuration of acyclic organic compounds was developed on the basis of carbon-proton spin-coupling constants and interproton spin-coupling constants. This method was developed for structural units represented by 2,3-or 2,4-disubstituted alkanes, where substituents were either dihydroxyl or methyl/hydroxyl groups. The basic theory of the methods is that, in acyclic systems, the conformation of adjacent asymmetric centers is represented by staggered rotamers, and their relative stereochemistry can be determined using these coupling constants because the combined use of the values enables the identification of the predominant staggered rotamer (s) out of the six possible ones derived from threo-and erythro-configuration. Detail conformational analysis for model and natural compounds, including maitotoxin, amphidinols and aflastatins, revealed that the method is practical for assignment of acyclic stereochemical centers.

Report

(4 results)
  • 2000 Annual Research Report   Final Research Report Summary
  • 1999 Annual Research Report
  • 1998 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Tanaka,I.: "A new ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate Coolia monotis."J.Nat.Prod.. 61. 685-688 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Murata,M.: "Labeling pattern of okadaic acid from ^<18>O_2 and [^<18>O_2]acetate elucidated by collision-induced dissociation tandem mass spectrometry."J.Am.Chem.Soc.. 120. 147-151 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Murata,M.: "Absolute configuration of amphidinol 3, the first complete structure determination from amphidinol homologues :"J.Am.Chem.Soc.. 121. 870-871 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Matsumori,N.: "Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants"J.Org.Chem.. 64. 866-876 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Izumikawa,M.: "^<18>O-labelling pattern of okadaic Acid from H_2^<18>O in dinoflagellate Prorocentrum lima elucidated by tandem mass spectrometry."Eur.J.Biochem... 267. 5179-5182 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Ikeda,H.: "Absolute configuration of alfatoxin A, a specific inhibitor of aflatoxin production by Aspergillus parasiticus"J.Org.Chem.. 65. 438-444 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Akasaka,K.: "Absolute configuration of a ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate, Coolia monotis."Biosci.Biotech.Biochem.. 64. 1842-1846 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Tanaka, I., Matsuoka, S., Murata, M.and Tachibana, K.: "A new ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate Coolia monotis."J.Nat.Prod.. 61. 685-688 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Murata, M., Izumikawa, M., Tachibana, K., Fujita, T.and Naoki, H.: "Labeling pattern of okadaic acid from ^<18>O_2 and [^<18>O_2] acetate elucidated by collision-induced dissociation tandem mass spectrometry."J.Am.Chem.Soc.. 120. 147-151 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Murata, M., Matsuoka, S., Matsumori, N., Paul, G.K., Tachibana, K.: "Absolute configuration of amphidinol 3, the first complete structure determination from amphidinol homologues : Application of a new configuration analysis based on the carbon-hydrogen spin-coupling constants."J.Am.Chem.Soc.. 121. 870-871 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Matsumori, N., Kaneno, D., Murata, M., Nakamura, H.and Tachibana, K.: "Stereochemical determination of acyclic structures based on carbon-proton spin-coupling constants -A method of configuration analysis for natural products."J.Org.Chem.. 64. 866-876 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Izumikawa, M., Murata, M., Tachibana, K., Fujita, T., Naoki, N.: "^<18>O-labelling pattern of okadaic Acid from H_2^<18>O in dinoflagellate Prorocentrum lima elucidated by tandem mass spectrometry."Eur.J.Biochem.. 267. 5179-5182 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Ikeda, H., Matsumotiri, N., Ono, M., Suzuki, A., Isogai, A, Nagasawa, H., Sakuda, S.: "Absolute configuration of alfatoxin A, a specific inhibitor of aflatoxin production by Aspergillus parasiticus"J.Org.Chem.. 65. 438-444 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] Akasaka, K., Shichijyukari, S., Matsuoka, S., Murata, M., H.Meguro, H.Ohrui.: "Absolute configuration of a ceramide with a novel branched-chain fatty acid isolated from the epiphytic dinoflagellate, Coolia monotis."Biosci.Biotech.Biochem.. 64. 1842-1846 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2000 Final Research Report Summary
  • [Publications] 赤坂和昭: "Absolute Configuration of a ceramide with a Novel Branched-chain Fatty Acid Isolated from the Epiphytic Dinoflagellate, Coolia monotis"Biosci. Biorech Biochem. 64. 1842 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] 泉川美穂: "^<18>O-labelling Pattern of Okadaic Acid from H_2 ^<18>O in Dinoflagellate Prorocentrum lima Elucidated by Tandem Mass Spectrometry."Eur.J.Biochem.. 267. 5179-5182 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Matsumori, N. et al.: "Stereochemical determination of acyclic structures based or carbon proton spin-coupling constants-A method of configuration analysis for natural product"J. Org. Chem.. 64. 866-876 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] Iijima, K. et al.: "Identification of N^ω-carboxymethylarginine as novel acid-labile advanced glycation and product in collagen"Biochemical. J.. (in press). (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] Michio Murata: "Absolute configuration of amphidinol 3,the first complete senucture elucidation from amphidinal nomolognes" Journal of American Chemical Society. 121. 870-871 (1999)

    • Related Report
      1998 Annual Research Report
  • [Publications] Nobuaki Matsumori: "Sterechemical determination of acyclic structures based on carbon-proton spin-compling constants-A method of condiguration analysis for natural products" The Journal of Organic Chemistry. (印刷中). (1999)

    • Related Report
      1998 Annual Research Report

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Published: 1998-04-01   Modified: 2016-04-21  

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