Hydrolytic and transglycosylation reactions of N-acyl modified substrates catalysed by β-N-acetylhexosaminidases

The hydrolytic and transglycosylation capabilities of 35 fungal beta-N-acetylhexosaminidases with p-nitrophenyl 2-amino-2deoxy-beta-D-glucopyranoside and its four N-acyl derivatives (CH=O, COCH2OH, COCH2CH3, COCF3) as substrates were tested. The preparation of four novel p-nitrophenyl disaccharides from these unnatural substrates catalysed by enzymes from Aspergillus oryzae, Penicillium oxalicum and Talaromyces flavus represents a considerable extension of the synthetic potential of glycosidases. (C) 2003 Elsevier Ltd. All rights reserved.