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

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F14%3A00433199" target="_blank" >RIV/61388971:_____/14:00433199 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1021/op400302b" target="_blank" >http://dx.doi.org/10.1021/op400302b</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/op400302b" target="_blank" >10.1021/op400302b</a>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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, andseries 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

Název v anglickém jazyce

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

Popis výsledku anglicky

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, andseries 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

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CE - Biochemie

OECD FORD obor

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Projekt

<a href="/cs/project/7E11011" target="_blank" >7E11011: Novel Biocatalysts for the Production of Glycosides</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2014

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Organic Process Research & Development

ISSN

1083-6160

e-ISSN

—

Svazek periodika

18

Číslo periodika v rámci svazku

6

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

7

Strana od-do

781-787

Kód UT WoS článku

000337870900015

EID výsledku v databázi Scopus

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