Effective chemoenzymatic synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide and analysis of their interactions with lectins

A convenient chemoenzymatic procedure for the synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide has been developed from p-nitrophenyl N-acetyl-β-d-glucosaminide as starting material through three steps: synthesis of p-nitrophenyl N-acetyllactosaminide with β-d-galactosidase, chemical reduction of the p-nitrophenyl group, and sialylation with sialyltransferase. The p-aminophenyl glycosides were then successfully biotin-labeled through the coupling with N-(+)-biotinyl-6-aminohexanoic acid to afford biotinylated oligosaccharides with an aminohexanosyl group and phenyl group as the spacers between the biotin and glycan. Furthermore, the biotin-labeled sugars were shown to be useful for immobilization and assay of the carbohydrate–lectin interactions by an optical biosensor based on surface plasmon resonance.