Synthetic Studies on Biologically Active Compounds Containing Pseudo-sugars
| Project/Area Number |
61550646
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Keio University |
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Principal Investigator |
OGAWA Seiichiro Faculty of Science and Technology, Keio University, 理工学部, 教授 (00051475)
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| Co-Investigator(Kenkyū-buntansha) |
TADANO Kin'ichi Faculty of Science and Technology, Keio University, 理工学部, 専任講師 (20051914)
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| Project Period (FY) |
1986 – 1987
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| Project Status |
Completed (Fiscal Year 1988)
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| 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)
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| Keywords | Pseudo-suagrs / Analogs of Antibiotics / アミノ配酸糖体抗生物質 / 擬似二糖類 |
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| 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.
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Report
(3 results)
Research Products
(12 results)
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[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,.
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