Kinetic Control of Regioselectivity in Glycosidase-catalysed Disaccharide Synthesis: Preparation of 2-Acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose (N,N'-diacetylchitobiose) and 2-Acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-gluco...

Article abstract of DOI:10.1039/c39940002227

During transfer of the N-acetyl-β-D-glucosaminyl (2-acetamido-2-deoxy-β-D-glucopyranosyl)residue from p-nitrophenyl N-acetyl-β-D-glucosaminide (p-nitrophenyl N-2-acetamido-2-deoxy-β-D-glucopyranoside) on to N-acetyl-D-glucosamine (2-acetamido-2-deoxy-D-glucopyranose) catalysed by the N-acetylhexosaminidase from Aspergillus oryzae, the major isomer formed was found to depend on the time course of the reaction, 1 -> 4 transfer predominating while the p-nitrophenyl glycoside was available as donor, but 1 -> 6 transfer when the initially-formed 1 -> 4 product took over as donor, results that could be interpreted in terms of a constant regioselectivity modulated by selective hydrolysis of the products.

Full text of DOI:10.1039/c39940002227

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