Synthesis of disaccharide derivatives employing β-N-acetyl-D-hexosaminidase, β-D-galactosidase and β-D-glucuronidase

beta-N-Acetyl-D-hexosaminidase from Aspergillus oryzae catalysed the stereo- and regiospecific formation of the 6-O-benzylated disaccharide derivatives GalNAc beta 1-3(6-OBn)Gal beta-SEt and GlcNAc beta l-3(6-OBn)Gal beta-SEt, which were obtained in transglycosylation reactions employing ethyl 6-O-benzyl-1-thio-beta-D-galactopyranoside as acceptor. Preparative amounts of the chitobiose derivative GlcNAc beta 1-3GlcNAc beta-OPhNO2-p was prepared as well. beta-N-Acetyl-D-hexosaminidase from bovine testes catalysed the specific synthesis of GlcNAc beta 1-3(6-OBn)GlcNH(2)beta-SEt and GalNAc beta 1-3(6-OBn)GlcNH(2)beta-SEt, employing ethyl 2-amino-6-O-benzyl-2-deoxy-1-thio-beta-D-glucopyranoside as acceptor. B-D-Glucuronidase from E. coli was found to catalyse the formation of GlcA beta 1-3(6-OBn)GlcNH(2)beta-SEt employing the same acceptor.