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BIOSYNTHTIC STUDY OF AERUGINOSINS FROM THE CYANOBACTERIA

Research Project

Project/Area Number 08456102
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Fisheries chemistry
Research InstitutionTHE UNIVERSITY OF TOKYO

Principal Investigator

MURAKAMI Msahiro  THE UNIVERSITY OF TOKYO,GRADUATE SCHOOL OF AGRICULTURAL AND LIFE SCIENCES,ASSOCIATE PROFESSOR, 大学院・農学生命科学研究科, 助教授 (70134517)

Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥7,700,000 (Direct Cost: ¥7,700,000)
Fiscal Year 1997: ¥2,300,000 (Direct Cost: ¥2,300,000)
Fiscal Year 1996: ¥5,400,000 (Direct Cost: ¥5,400,000)
KeywordsCyanobacteria / Microcystis / Oscillatoria / protease inhibitory compounds / aeruginosin / biosynthesis / Oscillatria
Research Abstract

Aeruginosins, which were produced by the cyanobacteria, were composed by three amino acids derivatives (Hpla ; p-hydroxy-phenyllactic acid, Choi ; 2-carboxy-6-hydroxyoctahydroindole and Arg derivatives) and one usual amino acid. These peptides showed strong protease inhibitory acyivities against trypsin, plasmin and thrombin.
In this study, I can not find the key compound of biosynthesis of aeruginosins, which was contained Arg at N-terminal of-peptide. But, the aeruginosins 102-A and -B,and the aeruginosin 103-A were isolated from the Microcystis viridis (NIES-102,103). These peptides possesed argininal at N-terminal. I also could isolate the aeruginosins 205-A and B from Oscillatoria agardhii (NIES-205), which were composed by agmatine, Choi, 3-hydroxyleucine, xylopyranose and Hpla. From these results, the biosynthetic pathway of aeruginosins was thought to be reducing pathway from Arg to argininal, argininol or agmatin. Unfortunately, the biosynthetic pathway of Choi could not be clearly defined from the incorpolation experience of labeled ^<13>C-Tyr.
Furthermore, I can clarified the aeruginosin 98-B's complete absolute stereostructure along with the mechanism of trypisn inhibition from the Xray analisis of the complex of trpsin and aeruginosin 98-B.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] Hisashi Matsuda et al.: "Aeruginosins 102-A and B,new thrombin inhibitors from the cyanobacterium Microcystisviridis(NIES-102)" Tetrahedron. 52(46). 14501-14506 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hee Jae Shin et al.: "Aeruginosins 205-A and B,serine protease inhibitory,glycopeptides from the cyanobacterium Oscillatoria agardhii(NIES-205)" J.Org.CHem.62(6). 1810-1813 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Benjamin Sandler et al.: "Atomic structure of the trypsin-aeruginosin 98-B complex" J.Am.Chem.Soc.120(3). 595-596 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Jorge L.Rios Ateiner et al.: "Structure of thrombin inhibited by aeruginosin 298-A from a blue-green alga" J.Am.Chem.Soc.120(3). 597-598 (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinya Kodani et al.: "Aeruginosin 103-A,a thrombin inhibitorfrom the cyanobacterium Microcystis viridis(NIES-103)" Tetrahedron Lett.(印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hisashi Matsuda, Tatsufumi Okino, Masahiro Murakami and Katsumi Yamaguchi: "Aeruginosins 102-A and B,new thrombin inhibitors from the cyanobacterium Microcystis viridis (NIES-102)" Tetrahedron. 52. 14501-14506 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hee Jae Shin, Hisashi Matsuda, Masahiro Murakami and Katsumi Yamaguchi: "Aeruginosins 205A and -B,serine protease inhibitory glycopeptides from the cyanobacterium Oscillatoria agardhii (NIES-205)" J.Org.Chem.62. 1810-1813 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Benjamin Sandler, Masahiro Murakami and Jon Clardy: "Atomic structure of the trypsin aeruginosin 98-B complex" J.Am.Chem.Soc.120. 595-596 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Jorge L.Rios, Masahiro Murakami and Alexander Tulinsky: "Structure of thrombin inhibited by aeruginosin 298-A from a blue-green alga" J.Am.Chem.Soc.120. 597-598 (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shinya Kodani, Keishi Ishida and Masahiro Murakami: "Aeruginosin 103-A,a thrombin inhibitor from the cyanobacterium Microcystis viridis (NIES-103)" Tetrahedron Lett. (Submitted).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Hee Jae Shin et al.: "Aeruginosins 205-A and B, serine protease inhibitory,glycopeptides from the cyanobacterium Oscillatoria agardhii(NIES-205)" J.Org .Chem.62(6). 1810-1813 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Jorge L.Rios Ateiner et al.: "Structure of thrombin inhibited by aeruginosin 298-A from a blue-green alga" J.Am.Chem.Soc.120(3). 597-598 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Benjamin Sandler et al.: "Atomic structure of the trypsin-aeruginosin 98-B complex" J.Am.Chem.Soc.120(3). 595-596 (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Shinya Kodani et al.: "Aeruginosin 103-A,a thrombin inhibitor from the cyanobacterium Microcystis viridis (NIES-l03)" Tetrahedron Lett.

    • Related Report
      1997 Annual Research Report
  • [Publications] Hee Jae Shin,他3名: "Aeruginosins 205-A and B,serine protease inhibitory glycopeptides from the cyanobacterium Oscillatoreia agardhii(NIES-205)" J.Organic.Chemistry. (発表予定). (1997)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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