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Biosynthesis of the chitinase inhibitor allosamidin produced by Streptomyces

Research Project

Project/Area Number 04660117
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 応用微生物学・発酵学
Research InstitutionOsaka University

Principal Investigator

YAMADA Yasuhiro  Osaka Univ. Fac, of Engineer. Prof., 工学部, 教授 (00011891)

Co-Investigator(Kenkyū-buntansha) SAKUDA Shohei  Osaka Univ. Fac, of Engineer. Associ. Prof., 工学部, 助手 (80192087)
NIHIYA Takuya  Osaka Univ. Fac, of Engineer. Associ. Prof., 工学部, 助教授 (70144441)
Project Period (FY) 1992 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1993: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1992: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsChitinase Inhibitor / allosamidin / Biosynthesis / Streptomyces / chitinase
Research Abstract

Allosamidin 1 is the first chitinase inhibitor produced by Streptomyces. The biosynthesis of 1, which has a novel trisaccharide structure and interesting biological activities, have been investigated.
1. a new allosamidin analog, didemethylallosamidin 3, was isolated from Streptomyces sp. Jj 9463 which is a producer of 1 and demethylallosamidin 2. ^<14>C-Labeled 1, 2 and 3 were prepared to investigate the biosythesis of 1. Comversion experiments with the labeled compounds revealed that 2 was a precursor of 1, but 3 was not incorporated. this suggests that the first N-methyl group is introduced before the cyclization of the aminooxazoline ring during the biosynthesis of 1.
2. Sllosamizoline 4 is a component of 1 and has a novel cyclopentanoid structure shich is biosynthesized form D-glucosamene. To study a mechanism of the cyclopentane ring formation of 4, feeding experiments with [4-^2H]-, [5-^2H][6-^2H_2]-D-glucosamine were carried out. ^2H NMR and Cl-MS analysis of the labeled samples indicated that loss of deuterium on C-5 and stereospecific loss of one of the two deuterium on C-6 of glucosamine occured during the biosynthesis. These results suggesed that the cyclization to from the cyclopentanoid moiety of 4 would proceed via an intermediate 6-aldehyde glucosamine derivative.
3. Two chitinases were purified form the culture filtrate of Streptomyces sp. AJ 9463. They had similar molecular masses and optimum pH rages, but showed quite different sensitivities to 1. The two chitinases and their genes might be useful probes to investigate the physiological significance of the co-production fo chitinases and its inhibitorin the strain.

Report

(3 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • Research Products

    (5 results)

All Other

All Publications (5 results)

  • [Publications] Qiuqi Wang: "Purification of allosamidin-sensitive and -insensitive chitinases produced by allosamidin-producing Streptomyces" Bioscience,Biotechnology,and Biochemistry. 57. 467-470 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Ze-Yang Zhou: "Biosynthetic studies of allosamidin 2.Isolation of didemethylallosamidin,and conversion experiments of ^<14>C-labeled demethylallosamidin,didemethylallosamidin and their related compounds." The Journal of Antibiotics. 46. 1582-1588 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Qiuqi Wang: "Purification of allosamidin-sensitive and -insensitive chitinases produced by allosamidin-producing Streptomyces" Bioscience, Biotechnology, and Biochemistry. 57. 467-470 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Ze-Yang Zhou: "Biosysthetic studies of allosamidin 2. lsolationof didemethylallosamidin, and conversion experiments of ^<14>C-labeled demethylallosamidin. didemethylallosamidin and their related compounds." The Journal of antibiotics. 46. 1582-1588 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Qiuqi Wang: "Purification of Allosamidin-sensitive and-insensitive Chitinases Produced by Allosamidin-producing Streptomyces" Bioscience,Biotechnology,and Biochemistry. 57. 467-470 (1993)

    • Related Report
      1992 Annual Research Report

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Published: 1992-04-01   Modified: 2016-04-21  

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