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Chemoenzymatic synthesis of neuraminic acid analogs structurally varied at C-5 and C-9 as potential inhibitors of the sialidase from influenza virus

✍ Scribed by Makoto Murakami; Kiyoshi Ikeda; Kazuo Achiwa

Book ID: 102993035
Publisher: Elsevier Science
Year: 1996
Tongue: English
Weight: 617 KB
Volume: 280
Category: Article
ISSN: 0008-6215
DOI: 10.1016/0008-6215(95)00295-2

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✦ Synopsis

The 9-amino or 9-N-acyl-5-trifluoroacetyl methyl alpha-ketosides (1a-c) and their 2,3-didehydro analogs (2a-c) have been synthesized through Neu5Ac aldolase-catalyzed aldol reaction of 6-azido-2-benzyloxycarbonylamino-2-deoxy-D-mannose with sodium pyruvate. The six compounds were investigated as inhibitors of sialidase from influenza virus. Compound 2b, a 2,3-didehydro type, showed the most potent inhibitory activity (IC50 > 7.8 microM) against the enzyme, whereas, compounds 1a-c as the methyl alpha-glycosides were found to be practically inactive (IC50 > 100 microM).

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