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Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase
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SYSNO ASEP 0433199 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase Author(s) De Winter, K. (BE)
Desmet, T. (BE)
Devlamynck, T. (BE)
Van Renterghem, L. (BE)
Verhaeghe, T. (BE)
Pelantová, Helena (MBU-M) ORCID, RID
Křen, Vladimír (MBU-M) RID, ORCID
Soetaert, W. (BE)Source Title Organic Process Research & Development. - : American Chemical Society - ISSN 1083-6160
Roč. 18, č. 6 (2014), s. 781-787Number of pages 7 s. Language eng - English Country US - United States Keywords biphasic systems ; pyrogallol ; biphasic catalysis Subject RIV CE - Biochemistry R&D Projects 7E11011 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Institutional support MBU-M - RVO:61388971 UT WOS 000337870900015 DOI 10.1021/op400302b Annotation 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 Workplace Institute of Microbiology Contact Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Year of Publishing 2015
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