An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors.
A novel approach to the synthesis of beta-glycosides of N-acetyl-D-glucosaminuronic acid, in six steps and good overall yield from N-acetyl-d-glucosamine, has been developed. The key synthetic step was the Lewis acid mediated O-glycosidation of methyl 1,3,4-tri-O-pivaloyl-N-acetyl-D-glucosaminuronate (11). Elaboration of glucosaminuronides 15 and 18 provided novel sialylmimetics 21 and 22, which showed inhibition of Vibrio cholerae sialidase.
Institute for Glycomics, Griffith University (Gold Coast Campus), PMB 50 Gold Coast Mail Centre, Queensland 9726, Australia.
Maretta C
MC
Mann
Robin J
RJ
Thomson
Mark
M
von Itzstein
D002236:Carbohydrate Conformation; D018716:Molecular Mimicry; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship; D014574:Uronic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014734:Vibrio cholerae / Q000201:enzymology
D014574:Uronic Acids; C497756:methyl 1,3,4-tri-O-pivaloyl-N-acetyl-D-glucosaminuronate; C000156:N-acetylglucosaminuronic acid; D009439:Neuraminidase