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Issue 16, 1996
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Glycosidase-catalysed oligosaccharide synthesis of di-, tri- and tetra-saccharides using the N-acetylhexosaminidase from Aspergillus oryzae and the β-galactosidase from Bacillus circulans

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 β-D-GlcpNAc-(1→6)-β-D-GalpNAc 3 thus synthesized acts as acceptor for transfer of a β-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 β-D-Galp-(1→4)-β-GlcpNAc-(1→6)-D-GalpNAc 8 in 48% yield together with the tetrasaccharide β-D-Galp-(1→4)-β-D-Gal-(1→4)-β-D-GlcpNAc-(1→6)-D-GalpNAc 9 in 7% yield. With lactose as acceptor, the trisaccharide β-D-Galp-(1→4)-β-D-Galp-(1→4)-D-Glcp 12, a growth factor for human intestinal bifidobacteria, is produced in 52% yield.p

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Article type: Paper
DOI: 10.1039/P19960001921
Citation: J. Chem. Soc., Perkin Trans. 1, 1996,0, 1921-1926

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

    S. Singh, M. Scigelova, G. Vic and D. H. G. Crout, J. Chem. Soc., Perkin Trans. 1, 1996, 0, 1921
    DOI: 10.1039/P19960001921

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