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Synthetic Studies on Biologically Active Compounds Containing Pseudo-sugars

Research Project

Project/Area Number 61550646
Research Category

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

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKeio University

Principal Investigator

OGAWA Seiichiro  Faculty of Science and Technology, Keio University, 理工学部, 教授 (00051475)

Co-Investigator(Kenkyū-buntansha) TADANO Kin'ichi  Faculty of Science and Technology, Keio University, 理工学部, 専任講師 (20051914)
Project Period (FY) 1986 – 1987
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1987: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1986: ¥1,000,000 (Direct Cost: ¥1,000,000)
KeywordsPseudo-suagrs / Analogs of Antibiotics / アミノ配酸糖体抗生物質 / 擬似二糖類
Research Abstract

Elucidation of the biological properties of pseudo-sugars, hexose analogs in which the pyranoid ring oxygen is replaced with the methylene group, may help to understand the roles that sugars play in biological systems. As part of a study of the synthesis of biologically active pseudo-sugar derivatives, the present study is concerned with the synthesis of the pseudo-sugar analogs of clinically important aminoglycoside antibiotics.
Trehalosamine is a simple aminoglycoside antibiotic produced by Streptomyces lavendulae. It is an , -(1 1)-linked disaccharide composed of D-glucose and 2-amino-2-deoxy-D-glucose. Three related compounds, the 3-amono-3-deoxy and 4-amino-4-deoxy isomers, and 2-amino-2-deoxy- -D-glucopyranosyl -D-mannopyranoside have been known so far. In this study, two stereoisomers of pseudo-tre-halosamine and four of glucopyranosyl mannopyranoside.
The pseudo-trehalosamine the absolute configuration of which corresponds that of natural antibiotic has shown to possess ca. 25% of the activity of 2-trehalosamine, and the other isomer was inactive. These results suggest that in biologically active oligosaccharides, replacement of the pyranoid-ring oxygen of one sugar residue with methylene group may not result in loss of activity. On the other hand, none of the isomers of the mannopyranoside had activity.

Report

(3 results)
  • 1988 Final Research Report Summary
  • 1987 Annual Research Report
  • 1986 Annual Research Report
  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] Seiichiro Ogawa.;Yasushi Shibata.: Carbohydrate Research. 170. 116-123 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Seiichiro Ogawa.;Yasushi Shibata.: Carbohydrate Research. 176. (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Seiichiro Ogawa.;Shigeki Yokoi,;Noritaka Kimura,;Yasushi Shibata.: Noritaka Chida Carbohydr.Res.,.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Ogawa, Seiichiro,; Shibata, Yasushi.: "Synthesis of Two Pseudo-sugar Analogues of 2-Amino-2-deoxy- D-glucopyranosyl -D-mannopyranoside" Carbohydrate Research. 170. 116-123 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Ogawa, Seiichiro,; Shibata, Yasushi.: "Synthesis of Biologically Active Pseudo-trehalosamine: [(1S)-(1,2,4/3,5)-2,3,4-Trihydroxy-5-hydroxymethyl-1-cyclohexyl] 2-amino-2-deoxy- -D-glucopyranoside" Carbohydrate Research. 176. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Ogawa, Seiichiro,; Yokoi, Shigeki,; Kimura, Noritaka,; Shibata, Yasushi,; Chida, Noritaka.: "Synthesis of Pseudo-trehaloses: [(1,2,4/3,5)-2,3,4-Trihydroxy-5-hydroxymethyl-1-cyclohexyl] D-glucopyranoside" Carbohydrate Research,.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Seiichiro Ogawa;Yasushi Shibata: Carbohydrate Research (Elsevier Science Publishers B. V., Amsterdam). 170. 116-123 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] Seiichiro Ogawa;Yasushi Shibata: Carbohydrate Research (Elsevier Science Publishers B. V., Amsterdam). 176. (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] Seiichiro Ogawa;Shigeki Yokio;Noritaka Kimura;Yasushi Shibata;Noritaka Chida: Carbohydrate Research (Elsevier Science Publishers B. V., Amsterdam). (1988)

    • Related Report
      1987 Annual Research Report
  • [Publications] Seiichiro Ogawa: Carbohydrate Research. 164. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Seiichiro Ogawa: Carbohydrate Research. 164. (1987)

    • Related Report
      1986 Annual Research Report
  • [Publications] Seiichiro Ogawa: Carbohydrate Research.

    • Related Report
      1986 Annual Research Report

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Published: 1987-03-31   Modified: 2016-04-21  

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