| 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)
|
|---|
| 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.
|
