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

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About: Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	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 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 (en)
Title	Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase (en)
skos:prefLabel	Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase Biphasic Catalysis with Disaccharide Phosphorylases: Chemoenzymatic Synthesis of alpha-D-Glucosides Using Sucrose Phosphorylase (en)
skos:notation	RIV/61388971:_____/14:00433199!RIV15-AV0-61388971
http://linked.open...avai/riv/aktivita	I P
http://linked.open...avai/riv/aktivity	I, P(7E11011)
http://linked.open...iv/cisloPeriodika	6
http://linked.open...vai/riv/dodaniDat	2015
http://linked.open...aciTvurceVysledku	Křen, Vladimír Pelantová, Helena
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Mikrobiologický ústav AV ČR, v. v. i.
http://linked.open...dnocenehoVysledku	5518
http://linked.open...ai/riv/idVysledku	RIV/61388971:_____/14:00433199
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	biphasic systems; pyrogallol; biphasic catalysis (en)
http://linked.open.../riv/klicoveSlovo	biphasic systems pyrogallol biphasic catalysis
http://linked.open...odStatuVydavatele	US - Spojené státy americké
http://linked.open...ontrolniKodProRIV	[0DA76131EBED]
http://linked.open...i/riv/nazevZdroje	Organic Process Research & Development
http://linked.open...in/vavai/riv/obor	CE
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	8 (xsd:int)
http://linked.open...vavai/riv/projekt	Novel Biocatalysts for the Production of Glycosides
http://linked.open...UplatneniVysledku	2014
http://linked.open...v/svazekPeriodika	18
http://linked.open...iv/tvurceVysledku	Křen, Vladimír Pelantová, Helena Desmet, T. Soetaert, W. De Winter, K. Devlamynck, T. Van Renterghem, L. Verhaeghe, T.
http://linked.open...ain/vavai/riv/wos	000337870900015
issn	1083-6160
number of pages	7 (xsd:int)
http://bibframe.org/vocab/doi	10.1021/op400302b

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