Kinetic Control of Regioselectivity in Glycosidase-catalyzed Disaccharide Synthesis - Preparation of 2-acetamido-4-o-(2-acetamido-2-deoxy-beta-d-glucopyranosyl)-2-deoxy-d-glucopyranose (n,n'-diacetylchitobiose) and 2-acetamido-6-o-(2-acetamido-2-deoxy-beta-d-glucopyranosyl)-2-deoxy-d-glucopyranose
Year: 2026
Type: article
Abstract: During transfer of the N-acetyl-D-glucosaminyl (2-acetamido-2-deoxy-beta-D-glucopyranosyl) residue from p-nitrophenyl N-acetyl-beta-D-glucosaminide (p-nitrophenyl N-2-acetamido-2-deoxy-beta-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.
Source: University of Warwick
Author: No author provided
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
OpenAlex ID: W7221103772