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.
Mann
Maretta C
MC
Institute for Glycomics, Griffith University (Gold Coast Campus), PMB 50 Gold Coast Mail Centre, Queensland 9726, Australia.
Thomson
Robin J
RJ
von Itzstein
Mark
M
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