Methyl α‐glycoside of N‐thioacetyl‐d‐neuraminic acid: A potential inhibitor of influenza A virus a 1H NMR study

Abstract
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 (1H 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.