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Glycosidase-catalysed oligosaccharide synthesis of di-, tri- and tetra-saccharides using the N-acetylhexosaminidase from Aspergillus oryzae and the beta-galactosidase from Bacillus circulans

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UNSPECIFIED (1996) Glycosidase-catalysed oligosaccharide synthesis of di-, tri- and tetra-saccharides using the N-acetylhexosaminidase from Aspergillus oryzae and the beta-galactosidase from Bacillus circulans. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 (16). pp. 1921-1926. ISSN 0300-922X

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Abstract

The N-acetylhexosaminidase from Aspergillus oryzae catalyse transfer of N-acetylglucosaminyl and N-acetylgalactosaminyl residues selectively on to the 6-OH group of N-acetylgalactosamine to give the corresponding (1-->6)-linked disaccharides 3 and 6 in 26 and 38% yield, respectively, The disaccharide beta-D-GlcpNAc-(1-->6)-beta-D-GalpNAc 3 thus synthesized acts as acceptor for transfer of a beta-D-galactosyl residue from the corresponding p-nitrophenyl glycoside on to the 4-OH group of the non-reducing unit to give the ovarian cyst fluid mucin fragment beta-D-Galp-(1-->4)-beta-GlcpNAc-(1-->6)-D-GalpNAc 8 in 48% yield together with the tetrasaccharide beta-D-Galp-(1-->4)-beta-D-Galp-(1-->4)-beta-D-GlcpNAc-(1-->6)-D-GalpNAc 9 in 7% yield, With lactose as acceptor, the trisaccharide beta-D-Galp-(1-->4)-beta-D-Galp-(1-->4)-D-Glcp 12, a growth factor for human intestinal bifidobacteria, is produced in 52% yield.

Item Type: Journal Article
Subjects: Q Science > QD Chemistry
Journal or Publication Title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Publisher: ROYAL SOC CHEMISTRY
ISSN: 0300-922X
Date: 21 August 1996
Number: 16
Number of Pages: 6
Page Range: pp. 1921-1926
Publication Status: Published
URI: http://wrap.warwick.ac.uk/id/eprint/18466

Data sourced from Thomson Reuters' Web of Knowledge

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