Abstract
AbstractCarbocyclic 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.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
