Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols

Halohydrin dehalogenases are usually recognized as strict β-position regioselective enzymes in the nucleophile-mediated ring-opening of epoxides. Here we found the HheG from Ilumatobacter coccineus exhibited excellent α-position regioselectivity in the azide-mediated ring-opening of styrene oxide de...

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Autores principales: An, Miao, Liu, Wanyi, Zhou, Xiaoying, Ma, Ran, Wang, Huihui, Cui, Baodong, Han, Wenyong, Wan, Nanwei, Chen, Yongzheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9064361/
https://www.ncbi.nlm.nih.gov/pubmed/35516406
http://dx.doi.org/10.1039/c9ra03774h
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author An, Miao
Liu, Wanyi
Zhou, Xiaoying
Ma, Ran
Wang, Huihui
Cui, Baodong
Han, Wenyong
Wan, Nanwei
Chen, Yongzheng
author_facet An, Miao
Liu, Wanyi
Zhou, Xiaoying
Ma, Ran
Wang, Huihui
Cui, Baodong
Han, Wenyong
Wan, Nanwei
Chen, Yongzheng
author_sort An, Miao
collection PubMed
description Halohydrin dehalogenases are usually recognized as strict β-position regioselective enzymes in the nucleophile-mediated ring-opening of epoxides. Here we found the HheG from Ilumatobacter coccineus exhibited excellent α-position regioselectivity in the azide-mediated ring-opening of styrene oxide derivatives 1a–1k, producing the corresponding 2-azido-2-aryl-1-ols 2a–2k with the yields up to 96%.
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spelling pubmed-90643612022-05-04 Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols An, Miao Liu, Wanyi Zhou, Xiaoying Ma, Ran Wang, Huihui Cui, Baodong Han, Wenyong Wan, Nanwei Chen, Yongzheng RSC Adv Chemistry Halohydrin dehalogenases are usually recognized as strict β-position regioselective enzymes in the nucleophile-mediated ring-opening of epoxides. Here we found the HheG from Ilumatobacter coccineus exhibited excellent α-position regioselectivity in the azide-mediated ring-opening of styrene oxide derivatives 1a–1k, producing the corresponding 2-azido-2-aryl-1-ols 2a–2k with the yields up to 96%. The Royal Society of Chemistry 2019-05-24 /pmc/articles/PMC9064361/ /pubmed/35516406 http://dx.doi.org/10.1039/c9ra03774h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
An, Miao
Liu, Wanyi
Zhou, Xiaoying
Ma, Ran
Wang, Huihui
Cui, Baodong
Han, Wenyong
Wan, Nanwei
Chen, Yongzheng
Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
title Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
title_full Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
title_fullStr Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
title_full_unstemmed Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
title_short Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
title_sort highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9064361/
https://www.ncbi.nlm.nih.gov/pubmed/35516406
http://dx.doi.org/10.1039/c9ra03774h
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