ISSN:
0947-3440
Keywords:
Carbohydrates
;
Pseudosugars
;
Cyclitols
;
Glycoceramide analogs
;
Lipids
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Carbocyclic analogs of glycoceramides, (2S,3R,4E)-1-(5a-carba-β-D-glycopyranosyl)-2-(hexadecanoylamino)-4-octa-decen-3-ols E-3-E-6, linked by imino, ether and sulfide bridges, were synthesized by coupling of aziridines, as the sphingosine precursors, with protected 1-amino, 1-hydroxy and 1-mercapto derivatives of 5a-carba sugars and subsequent deprotection and N-acylation. Biological assay of 5a-carbaglycosylceramides showed that both imino-linked E-3 and E-4 having gluco and galacto configurations are mild immunomodulators and possess a mild inhibitory activity against gluco- and galactocerebrosidases. These findings prompted us to prepare the corresponding Z-isomers Z-3 and Z-4, which interestingly show a similar enzyme-inhibitory activity.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199519950236
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