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.
Biochem Biophys Res Commun, 1997/5/19;234(2):358-61.
Vetere A[1], Galateo C, Paoletti S
Affiliations
PMID: 9177275
Impact factor: 3.322
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.
MeSH terms
Aspergillus niger; Carbohydrate Conformation; Carbohydrate Sequence; Chromatography, High Pressure Liquid; Disaccharides; Glycosylation; Lewis X Antigen; Magnetic Resonance Spectroscopy; Mass Spectrometry; Molecular Sequence Data; Molecular Structure; Oligosaccharides; Water; alpha-L-Fucosidase
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