1-O-Acetyl-beta-D-galactopyranose: a novel substrate for the transglycosylation reaction catalyzed by the beta-galactosidase from Penicillium sp

Carbohydrate Research
Alexander I ZininK N Neustroev

Abstract

1-O-Acetyl-beta-D-galactopyranose (AcGal), a new substrate for beta-galactosidase, was synthesized in a stereoselective manner by the trichloroacetimidate procedure. Kinetic parameters (K(M) and k(cat)) for the hydrolysis of 1-O-acetyl-beta-D-galactopyranose catalyzed by the beta-D-galactosidase from Penicillium sp. were compared with similar characteristics for a number of natural and synthetic substrates. The value for k(cat) in the hydrolysis of AcGal was three orders of magnitude greater than for other known substrates. The beta-galactosidase hydrolyzes AcGal with retention of anomeric configuration. The transglycosylation activity of the beta-D-galactosidase in the reaction of AcGal and methyl beta-D-galactopyranoside (1) as substrates was investigated by 1H NMR spectroscopy and HPLC techniques. The transglycosylation product using AcGal as a substrate was beta-D-galactopyranosyl-(1-->6)-1-O-acetyl-beta-D-galactopyranose (with a yield of approximately 70%). In the case of 1 as a substrate, the main transglycosylation product was methyl beta-D-galactopyranosyl-(1-->6)-beta-D-galactopyranoside. Methyl beta-D-galactopyranosyl-(1-->3)-beta-D-galactopyranoside was found to be minor product in the latter reaction.

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Citations

Aug 5, 2009·Acta Crystallographica. Section F, Structural Biology and Crystallization Communications·Mirko MaksimainenJuha Rouvinen
Aug 12, 2014·Journal of Plant Physiology·Masahiro EdaKenneth C Gross
Feb 11, 2015·Acta Crystallographica. Section F, Structural Biology Communications·Masahiro EdaToshiji Tada
Aug 12, 2019·Applied Microbiology and Biotechnology·Pavla BojarováVladimír Křen
May 30, 2017·Chemical Science·David Lim, Antony J Fairbanks
Oct 20, 2004·Journal of Molecular Biology·A L RojasI Polikarpov
Jan 4, 2022·Journal, Genetic Engineering & Biotechnology·Mario A Mejía-MendozaJosé Francisco Morales-Domínguez

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