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An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors.

Mann, Maretta C; Thomson, Robin J; von Itzstein, Mark.
Bioorg Med Chem Lett; 14(22): 5555-8, 2004 Nov 15.
Artigo em Inglês | MEDLINE | ID: mdl-15482923
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.
Selo DaSilva