A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols

[Image: see text] A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonrea...

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Autores principales: Schober, Markus, Gadler, Petra, Knaus, Tanja, Kayer, Heidemarie, Birner-Grünberger, Ruth, Gülly, Christian, Macheroux, Peter, Wagner, Ulrike, Faber, Kurt
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2011
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155277/
https://www.ncbi.nlm.nih.gov/pubmed/21770430
http://dx.doi.org/10.1021/ol201635y
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author Schober, Markus
Gadler, Petra
Knaus, Tanja
Kayer, Heidemarie
Birner-Grünberger, Ruth
Gülly, Christian
Macheroux, Peter
Wagner, Ulrike
Faber, Kurt
author_facet Schober, Markus
Gadler, Petra
Knaus, Tanja
Kayer, Heidemarie
Birner-Grünberger, Ruth
Gülly, Christian
Macheroux, Peter
Wagner, Ulrike
Faber, Kurt
author_sort Schober, Markus
collection PubMed
description [Image: see text] A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale.
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spelling pubmed-31552772011-08-12 A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols Schober, Markus Gadler, Petra Knaus, Tanja Kayer, Heidemarie Birner-Grünberger, Ruth Gülly, Christian Macheroux, Peter Wagner, Ulrike Faber, Kurt Org Lett [Image: see text] A metallo-β-lactamase-type alkylsulfatase was found to catalyze the enantioselective hydrolysis of sec-alkylsulfates with strict inversion of configuration. This catalytic event, which does not have an analog in chemocatalysis, yields homochiral (S)-configurated alcohols and nonreacted sulfate esters. The latter could be converted into (S)-sec-alcohols as the sole product in up to >99% ee via a chemoenzymatic deracemization protocol on a preparative scale. American Chemical Society 2011-07-19 2011-08-19 /pmc/articles/PMC3155277/ /pubmed/21770430 http://dx.doi.org/10.1021/ol201635y Text en Copyright © 2011 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Schober, Markus
Gadler, Petra
Knaus, Tanja
Kayer, Heidemarie
Birner-Grünberger, Ruth
Gülly, Christian
Macheroux, Peter
Wagner, Ulrike
Faber, Kurt
A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols
title A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols
title_full A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols
title_fullStr A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols
title_full_unstemmed A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols
title_short A Stereoselective Inverting sec-Alkylsulfatase for the Deracemization of sec-Alcohols
title_sort stereoselective inverting sec-alkylsulfatase for the deracemization of sec-alcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3155277/
https://www.ncbi.nlm.nih.gov/pubmed/21770430
http://dx.doi.org/10.1021/ol201635y
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