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Methyl α‐glycoside of N ‐thioacetyl‐ d ‐neuraminic acid: A potential inhibitor of influenza A virus a 1 H NMR study
Author(s) -
Machytka Daisy,
Kharitonenkov Igor,
Isecke Rainer,
Hetterich Peter,
Brossmer Reinhard,
Klein Roger A,
Klenk Hans-Dieter,
Egge Heinz
Publication year - 1993
Publication title -
febs letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.593
H-Index - 257
eISSN - 1873-3468
pISSN - 0014-5793
DOI - 10.1016/0014-5793(93)81694-u
Subject(s) - neuraminic acid , sialic acid , chemistry , dissociation constant , stereochemistry , nuclear magnetic resonance spectroscopy , glycoside , hemagglutinin (influenza) , biochemistry , receptor , gene
The binding of influenza A virus hemagglutinin to its cell surface receptor, α‐linked 5‐ N ‐acetylneuraminic acid (sialic acid), was studied in solution. The effect of structural modifications introduced into the N ‐acetyl group of the sialic acid on the binding was monitored by determining the dissociation constants by proton nuclear magnetic resonance ( 1 H NMR) spectroscopy. Methyl α‐glycoside of N ‐thioacetylneuraminic acid showed high, whereas the corresponding N ‐methylcarbamoylneuraminic acid exhibited relatively low binding affinity towards the hemagglutinin.