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