title: Fluorescent ligands for the hemagglutinin of influenza A: synthesis and ligand binding assays.
abstract: 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.
authors.affiliation: MRC National Institute for Medical Research, The Ridgeway, Mill Hill, London NW7 1AA, UK.
authors.forename: V Ranjit N
authors.initials: VR
authors.lastname: Munasinghe
authors.forename: John E T
authors.initials: JE
authors.lastname: Corrie
authors.forename: Geoff
authors.initials: G
authors.lastname: Kelly
authors.forename: Stephen R
authors.initials: SR
authors.lastname: Martin
mesh_terms: 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
chemical_list: D005456:Fluorescent Dyes; D019267:Hemagglutinin Glycoproteins, Influenza Virus; D008024:Ligands