ISSN:
0170-2041
Keywords:
Carbohydrates
;
Pseudosugars
;
Cyclitols
;
Glycolipid analogs
;
Lipids, cyclitol
;
Glycosylamides, 5a-carba-
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199419940202
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