2-Substituted methyl alpha-D-galactopyranosides: synthesis and binding affinity for the A and B subunits of the Griffonia simplicifolia I isolectins.
The binding affinities of the N-acetyl, N-trifluoroacetyl, N-propionyl, N-formyl, N-benzoyl, N-p-nitrobenzoyl, N-p-aminobenzoyl, and N-methyl derivatives of methyl 2-amino-2-deoxy-alpha-D-galactopyranoside and the 2-O-acetyl, -benzoyl, -benzyl, and -methyl derivatives of methyl alpha-D-galactopyranoside for the A and B subunits of the Griffonia simplicifolia I isolectins have been determined by hapten inhibition analysis of a galactomannan-isolectin precipitation system. Models for these carbohydrate-protein interactions are presented together with an interpretation of the results on the basis of electronic and steric effects.
D006241:Haptens; D007202:Indicators and Reagents; D037102:Lectins; D046911:Macromolecular Substances; D009682:Magnetic Resonance Spectroscopy; D008756:Methylgalactosides / Q000138:chemical synthesis*; D008759:Methylglycosides / Q000138:chemical synthesis*; D009904:Optical Rotation; D013329:Structure-Activity Relationship
D006241:Haptens; D007202:Indicators and Reagents; D037102:Lectins; D046911:Macromolecular Substances; D008756:Methylgalactosides; D008759:Methylglycosides