Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase

0433199 - MBÚ 2015 RIV US eng J - Journal Article
De Winter, K. - Desmet, T. - Devlamynck, T. - Van Renterghem, L. - Verhaeghe, T. - Pelantová, Helena - Křen, Vladimír - Soetaert, W.
Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase.
Organic Process Research & Development. Roč. 18, č. 6 (2014), s. 781-787. ISSN 1083-6160. E-ISSN 1520-586X
R&D Projects: GA MŠMT(CZ) 7E11011
Institutional support: RVO:61388971
Keywords : biphasic systems * pyrogallol * biphasic catalysis
Subject RIV: CE - Biochemistry
Impact factor: 2.528, year: 2014

Thanks to its broad acceptor specificity, sucrose phosphorylase (SP) has been exploited for the transfer of glucose to a wide variety of acceptor molecules. Unfortunately, the low affinity (K-m > 1 M) of SP towards these acceptors typically urges the addition of cosolvents, which often either fail to dissolve sufficient substrate or progressively give rise to enzyme inhibition and denaturation. In this work, a buffer/ethyl acetate ratio of 5:3 was identified to be the optimal solvent system, allowing the use of SP in biphasic systems. Careful optimization of the reaction conditions enabled the synthesis of a range of alpha-D-glucosides, such as cinnamyl alpha-D-glucopyranoside, geranyl alpha-D-glucopyranoside, 2-O-alpha-D-glucopyranosyl pyrogallol, and series of alkyl gallyl 4-O-alpha-D-glucopyranosides. The usefulness of biphasic catalysis was further illustrated by comparing the glucosylation of pyrogallol in a cosolvent and biphasic reaction system. The acceptor yield for the former reached only 17.4%, whereas roughly 60% of the initial pyrogallol was converted when using biphasic catalysis
Permanent Link: http://hdl.handle.net/11104/0237459