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Statements

Subject Item
n2:RIV%2F61388971%3A_____%2F14%3A00433199%21RIV15-AV0-61388971
rdf:type
n12:Vysledek skos:Concept
dcterms: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
dcterms: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
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
skos:notation
RIV/61388971:_____/14:00433199!RIV15-AV0-61388971
n5:aktivita
n13:P n13:I
n5:aktivity
I, P(7E11011)
n5:cisloPeriodika
6
n5:dodaniDat
n9:2015
n5:domaciTvurceVysledku
n11:7346689 n11:5894190
n5:druhVysledku
n14:J
n5:duvernostUdaju
n15:S
n5:entitaPredkladatele
n6:predkladatel
n5:idSjednocenehoVysledku
5518
n5:idVysledku
RIV/61388971:_____/14:00433199
n5:jazykVysledku
n8:eng
n5:klicovaSlova
biphasic systems; pyrogallol; biphasic catalysis
n5:klicoveSlovo
n7:biphasic%20catalysis n7:biphasic%20systems n7:pyrogallol
n5:kodStatuVydavatele
US - Spojené státy americké
n5:kontrolniKodProRIV
[0DA76131EBED]
n5:nazevZdroje
Organic Process Research & Development
n5:obor
n18:CE
n5:pocetDomacichTvurcuVysledku
2
n5:pocetTvurcuVysledku
8
n5:projekt
n16:7E11011
n5:rokUplatneniVysledku
n9:2014
n5:svazekPeriodika
18
n5:tvurceVysledku
Pelantová, Helena Křen, Vladimír Van Renterghem, L. De Winter, K. Desmet, T. Devlamynck, T. Soetaert, W. Verhaeghe, T.
n5:wos
000337870900015
s:issn
1083-6160
s:numberOfPages
7
n17:doi
10.1021/op400302b