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

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Abstract

The synthesis of Neu5Ac2en mimetics as inhibitors of Vibrio cholerae sialidase is reported. A novel approach to the synthesis of β-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. © 2004 Elsevier Ltd. All rights reserved.

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Mann, M. C., Thomson, R. J., & Von Itzstein, M. (2004). An efficient approach to N-acetyl-D-glucosaminuronic acid-based sialylmimetics as potential sialidase inhibitors. Bioorganic and Medicinal Chemistry Letters, 14(22), 5555–5558. https://doi.org/10.1016/j.bmcl.2004.08.064

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