Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes

The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes...

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Detalles Bibliográficos
Autores principales: Demming, Rebecca M., Hammer, Stephan C., Nestl, Bettina M., Gergel, Sebastian, Fademrecht, Silvia, Pleiss, Jürgen, Hauer, Bernhard
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2018
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471033/
https://www.ncbi.nlm.nih.gov/pubmed/30256501
http://dx.doi.org/10.1002/anie.201810005
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author Demming, Rebecca M.
Hammer, Stephan C.
Nestl, Bettina M.
Gergel, Sebastian
Fademrecht, Silvia
Pleiss, Jürgen
Hauer, Bernhard
author_facet Demming, Rebecca M.
Hammer, Stephan C.
Nestl, Bettina M.
Gergel, Sebastian
Fademrecht, Silvia
Pleiss, Jürgen
Hauer, Bernhard
author_sort Demming, Rebecca M.
collection PubMed
description The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee, >95 % regioselectivity), and on a preparative scale.
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spelling pubmed-64710332019-04-19 Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes Demming, Rebecca M. Hammer, Stephan C. Nestl, Bettina M. Gergel, Sebastian Fademrecht, Silvia Pleiss, Jürgen Hauer, Bernhard Angew Chem Int Ed Engl Communications The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long‐standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion, excellent selectivity (>99 % ee, >95 % regioselectivity), and on a preparative scale. John Wiley and Sons Inc. 2018-11-30 2019-01-02 /pmc/articles/PMC6471033/ /pubmed/30256501 http://dx.doi.org/10.1002/anie.201810005 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Communications
Demming, Rebecca M.
Hammer, Stephan C.
Nestl, Bettina M.
Gergel, Sebastian
Fademrecht, Silvia
Pleiss, Jürgen
Hauer, Bernhard
Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
title Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
title_full Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
title_fullStr Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
title_full_unstemmed Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
title_short Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
title_sort asymmetric enzymatic hydration of unactivated, aliphatic alkenes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6471033/
https://www.ncbi.nlm.nih.gov/pubmed/30256501
http://dx.doi.org/10.1002/anie.201810005
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