Methyl alpha-glycoside of N-thioacetyl-D-neuraminic acid: a potential inhibitor of influenza A virus. A 1H NMR study.
The binding of influenza A virus hemagglutinin to its cell surface receptor, alpha-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 alpha-glycoside of N-thioacetylneuraminic acid showed high, whereas the corresponding N-methylcarbamoylneuraminic acid exhibited relatively low binding affinity towards the hemagglutinin.
Machytka
D
D
Physiologisch-Chemisches Institut, Universität Bonn, Germany.
Kharitonenkov
I
I
Isecke
R
R
Hetterich
P
P
Brossmer
R
R
Klein
R A
RA
Klenk
H D
HD
Egge
H
H
D004591:Electrophoresis, Polyacrylamide Gel; D006027:Glycosides / Q000494:pharmacology*; D019267:Hemagglutinin Glycoproteins, Influenza Virus; D006389:Hemagglutinins, Viral / Q000378:metabolism; D009980:Influenza A virus / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D019158:N-Acetylneuraminic Acid; D009438:Neuraminic Acids / Q000737:chemistry / Q000494:pharmacology*; D012794:Sialic Acids / Q000378:metabolism; D012996:Solutions
D006027:Glycosides; D019267:Hemagglutinin Glycoproteins, Influenza Virus; D006389:Hemagglutinins, Viral; D009438:Neuraminic Acids; D012794:Sialic Acids; D012996:Solutions; D019158:N-Acetylneuraminic Acid