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

Xiaoxiong Zeng, Yi Sun, Hong Ye, Jun Liu, Xiaoli Xiang, Bei Zhou, Hirotaka Uzawa

Index: Carbohydr. Res. 342 , 1244-1248, (2007)

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Abstract

A convenient chemoenzymatic procedure for the synthesis of p-aminophenyl glycosides of sialyl N-acetyllactosaminide has been developed from p-nitrophenyl N-acetyl-beta-D-glucosaminide as starting material through three steps: synthesis of p-nitrophenyl N-acetyllactosaminide with beta-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.