Enantioselective Bio-Hydrolysis of Various Racemic and meso Aromatic Epoxides Using the Recombinant Epoxide Hydrolase Kau2

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F15%3A00445870" target="_blank" >RIV/61388971:_____/15:00445870 - isvavai.cz</a>

Výsledek na webu

<a href="http://dx.doi.org/10.1002/adsc.201401164" target="_blank" >http://dx.doi.org/10.1002/adsc.201401164</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/adsc.201401164" target="_blank" >10.1002/adsc.201401164</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Enantioselective Bio-Hydrolysis of Various Racemic and meso Aromatic Epoxides Using the Recombinant Epoxide Hydrolase Kau2

Popis výsledku v původním jazyce

Epoxide hydrolase Kau2 overexpressed in Escherichia coli RE3 has been tested with ten different racemic and meso alpha,beta-disubstituted aromatic epoxides. Some of the tested substrates were bi-functional, and most of them are very useful building blocks in synthetic chemistry applications. As a general trend Kau2 proved to be an extremely enantioselective biocatalyst, the diol products and remaining epoxides of the bioconversions being obtained - with two exceptions - in nearly enantiomerically pure form. Furthermore, the reaction times were usually very short (around 1 h, except when stilbene oxides were used), and the use of organic co-solvents was well tolerated, enabling very high substrate concentrations (up to 75 g/L) to be reached. Even extremely sterically demanding epoxides such as cis- and trans-stilbene oxides were transformed on a reasonable time scale. All reactions were successfully conducted on a 1 g preparative scale, generating diol-and epoxide-based chiral synthons

Název v anglickém jazyce

Enantioselective Bio-Hydrolysis of Various Racemic and meso Aromatic Epoxides Using the Recombinant Epoxide Hydrolase Kau2

Popis výsledku anglicky

Epoxide hydrolase Kau2 overexpressed in Escherichia coli RE3 has been tested with ten different racemic and meso alpha,beta-disubstituted aromatic epoxides. Some of the tested substrates were bi-functional, and most of them are very useful building blocks in synthetic chemistry applications. As a general trend Kau2 proved to be an extremely enantioselective biocatalyst, the diol products and remaining epoxides of the bioconversions being obtained - with two exceptions - in nearly enantiomerically pure form. Furthermore, the reaction times were usually very short (around 1 h, except when stilbene oxides were used), and the use of organic co-solvents was well tolerated, enabling very high substrate concentrations (up to 75 g/L) to be reached. Even extremely sterically demanding epoxides such as cis- and trans-stilbene oxides were transformed on a reasonable time scale. All reactions were successfully conducted on a 1 g preparative scale, generating diol-and epoxide-based chiral synthons

Druh

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

CEP obor

CE - Biochemie

OECD FORD obor

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Projekt

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Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2015

Kód důvěrnosti údajů

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

Název periodika

Advanced Synthesis & Catalysis

ISSN

1615-4150

e-ISSN

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Svazek periodika

357

Číslo periodika v rámci svazku

8

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

14

Strana od-do

1895-1908

Kód UT WoS článku

000355235700029

EID výsledku v databázi Scopus

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