Fluorescent ligands for the hemagglutinin of influenza A: synthesis and ligand binding assays.
Two fluorescent conjugates of sialic acid have been prepared, with a convenient synthetic route that involves preparation of an unsaturated benzyl ester by cross-metathesis, followed by combined hydrogenation/ hydrogenolysis to provide a sialoside bearing a delta-carboxybutyl group, suitable for coupling with the chosen fluorophores. The fluorescent conjugates bound to bromelain-cleaved hemagglutinin (BHA) with affinities in the low microM range. Binding was accompanied by approximately 4.5-fold fluorescence enhancement for the dansyl conjugate 1 and approximately 3-fold fluorescence quenching for the pyrene conjugate 3.
Munasinghe
V Ranjit N
VR
MRC National Institute for Medical Research, The Ridgeway, Mill Hill, London NW7 1AA, UK.
Corrie
John E T
JE
Kelly
Geoff
G
Martin
Stephen R
SR
D005456:Fluorescent Dyes / Q000737:chemistry*; D019267:Hemagglutinin Glycoproteins, Influenza Virus / Q000032:analysis* / Q000737:chemistry*; D009980:Influenza A virus / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure
D005456:Fluorescent Dyes; D019267:Hemagglutinin Glycoproteins, Influenza Virus; D008024:Ligands