N-Acetylglucosaminyl Disaccharide and Trisaccharide Formation Through Lysozyme-Catalyzed Transfer Reaction

A hen egg-white lysozyme produced regioselectively 4-O-(2-acetamido–2-deoxy-β-D-glucopyranosyl)-D-mannose and p-nitrophenyl 4-O-(2-acet-amido–2-deoxy-β-D-glucopyranosyl)-β-D-mannopyranoside through a transglycosylation reaction from N,N′-diacetylchitobiose and respectively mannose and p-nitrophenyl β-D-mannopyranoside. These enzyme reactions were efficient enough to allow the one-pot preparation of the desired disaccharide. When p-nitrophenyl 2-acetamido-2-deoxy-α-D-glucopyranoside was the acceptor, the enzyme catalyzed the formation of a β-(1–3)-linked disaccharide glycoside (p-nitrophenyl 2-acetamido-2-deoxy-3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl) α-D-glucopyranoside) with its β-(1–4)-linked isomer. This is also the case for the formation of p-nitrophenyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-α-maltoside with p-nitrophenyl α-maltoside acceptor. The results show that the anomeric configuration of the glycosidic linkage in the glycosyl acceptors had a pronounced effect on the position of transglycosylation.