All-aqueous, regiospecific transglycosylation synthesis of 3-O-alpha-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a building block for the synthesis of branched oligosaccharides.

doi:10.1006/BBRC.1997.6630

Paper

All-aqueous, regiospecific transglycosylation synthesis of 3-O-alpha-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a building block for the synthesis of branched oligosaccharides.

Published May 19, 1997 · A. Vetere, C. Galateo, S. Paoletti

Biochemical and biophysical research communications

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21

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Abstract

A transglycosylation reaction, carried out in an aqueous medium and catalyzed by a crude preparation of alpha-fucosidase (E.C. 3.2.1.51) from Aspergillus niger, allowed for the regiospecific synthesis of the disaccharide 3-O-alpha-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose using p-nitrophenyl-alpha-L-fucopyranose as the donor and 2-acetamido-2-deoxy-D-glucopyranose as the acceptor. The chemical identity of the product obtained was demonstrated by HPLC, ion spray mass spectrometry and NMR spectroscopy. Further transglycosylation using a beta-galactosidase (E.C. 3.2.1.23) yielded the branched oligosaccharide 2-acetamido-2-deoxy-3-O-(alpha-L-fucopyranosyl)-4-O-(beta-D-galactopyran osyl)-D-glucopyranose, i.e., the Lewis(x) antigen.

Study Snapshot

This study demonstrates a regiospecific transglycosylation reaction for the synthesis of 3-O-alpha-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a building block for the synthesis of branched

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

All-aqueous, regiospecific transglycosylation synthesis of 3-O-alpha-L-fucopyranosyl-2-acetamido-2-deoxy-D-glucopyranose, a building block for the synthesis of branched oligosaccharides.

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