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Pseudosugars, 33. Synthesis of some 5a-carbaglycosylamides, glycolipid analogs of biological interests

✍ Scribed by Tsunoda, Hidetoshi ;Ogawa, Seiichiro

Book ID
102901942
Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
577 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Five carbocyclic analogs of glycosylamides, N‐(5a‐carba‐D‐glycopyranosyl)‐N‐octadecyldodecanamides 2–6, having β‐galacto, α‐ and β‐gluco‐, and α‐ and β‐manno configurations, were synthesized by coupling of the protected anhydro derivatives 12, 15, and 21 of 5a‐carba‐sugars with octadecylamine, followed by N‐acylation. Walden inversion of the 2‐OH functions of 17 and 24 was carried out through O‐sulfonylation. A bioassay (in vivo) of 5a‐carbaglycosylamides showed that they are potent immunomodulators, obviously comparable to the true sugar analogs, suggesting that the 5acarbasugar analogs may provide appropriate model compounds for biochemical studies in glycolipid chemistry. magnified image

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