Nitrite-mediated hydrolysis of epoxides catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1: A new tool for the kinetic resolution of epoxides

Ghania Hasnaoui; Jeffrey H. Lutje Spelberg; Erik de Vries; Lixia Tang; Bernhard Hauer; Dick B. Janssen

doi:10.1016/j.tetasy.2005.03.021

Nitrite-mediated hydrolysis of epoxides catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1: A new tool for the kinetic resolution of epoxides

Ghania Hasnaoui, Jeffrey H. Lutje Spelberg, Erik de Vries, Lixia Tang, Bernhard Hauer, Dick B. Janssen

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Abstract

Halohydrin dehalogenase obtained from Agrobacterium radiobacter AD1, has been tested for the nitrite-mediated ring opening of epoxides. This reaction mainly leads to the formation of unstable hydroxynitrite ester intermediates, which can be further hydrolyzed to the corresponding diols. This conversion proceeds with high enantioselectivity and high regioselectivity towards styrene oxide derivatives. It has been concluded that halohydrin dehalogenase can serve as an attractive alternative to epoxide hydrolases in the preparation of enantiopure epoxides by kinetic resolution.

Original language	English
Pages (from-to)	1685-1692
Number of pages	8
Journal	Tetrahedron: Assymmetry
Volume	16
Issue number	9
DOIs	https://doi.org/10.1016/j.tetasy.2005.03.021
Publication status	Published - 2-May-2005

Keywords

ALKYL NITRITES

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title = "Nitrite-mediated hydrolysis of epoxides catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1: A new tool for the kinetic resolution of epoxides",

abstract = "Halohydrin dehalogenase obtained from Agrobacterium radiobacter AD1, has been tested for the nitrite-mediated ring opening of epoxides. This reaction mainly leads to the formation of unstable hydroxynitrite ester intermediates, which can be further hydrolyzed to the corresponding diols. This conversion proceeds with high enantioselectivity and high regioselectivity towards styrene oxide derivatives. It has been concluded that halohydrin dehalogenase can serve as an attractive alternative to epoxide hydrolases in the preparation of enantiopure epoxides by kinetic resolution.",

keywords = "ALKYL NITRITES",

author = "Ghania Hasnaoui and {Lutje Spelberg}, {Jeffrey H.} and {de Vries}, Erik and Lixia Tang and Bernhard Hauer and Janssen, {Dick B.}",

note = "Relation: http://www.rug.nl/gbb/ date_submitted:2009 Rights: University of Groningen, Groningen Biomolecular Sciences and Biotechnology Institute",

year = "2005",

month = may,

day = "2",

doi = "10.1016/j.tetasy.2005.03.021",

language = "English",

volume = "16",

pages = "1685--1692",

journal = "Tetrahedron: Assymmetry",

issn = "0957-4166",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

number = "9",

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TY - JOUR

T1 - Nitrite-mediated hydrolysis of epoxides catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1

T2 - A new tool for the kinetic resolution of epoxides

AU - Hasnaoui, Ghania

AU - Lutje Spelberg, Jeffrey H.

AU - de Vries, Erik

AU - Tang, Lixia

AU - Hauer, Bernhard

AU - Janssen, Dick B.

N1 - Relation: http://www.rug.nl/gbb/ date_submitted:2009 Rights: University of Groningen, Groningen Biomolecular Sciences and Biotechnology Institute

PY - 2005/5/2

Y1 - 2005/5/2

N2 - Halohydrin dehalogenase obtained from Agrobacterium radiobacter AD1, has been tested for the nitrite-mediated ring opening of epoxides. This reaction mainly leads to the formation of unstable hydroxynitrite ester intermediates, which can be further hydrolyzed to the corresponding diols. This conversion proceeds with high enantioselectivity and high regioselectivity towards styrene oxide derivatives. It has been concluded that halohydrin dehalogenase can serve as an attractive alternative to epoxide hydrolases in the preparation of enantiopure epoxides by kinetic resolution.

AB - Halohydrin dehalogenase obtained from Agrobacterium radiobacter AD1, has been tested for the nitrite-mediated ring opening of epoxides. This reaction mainly leads to the formation of unstable hydroxynitrite ester intermediates, which can be further hydrolyzed to the corresponding diols. This conversion proceeds with high enantioselectivity and high regioselectivity towards styrene oxide derivatives. It has been concluded that halohydrin dehalogenase can serve as an attractive alternative to epoxide hydrolases in the preparation of enantiopure epoxides by kinetic resolution.

KW - ALKYL NITRITES

U2 - 10.1016/j.tetasy.2005.03.021

DO - 10.1016/j.tetasy.2005.03.021

M3 - Article

SN - 0957-4166

VL - 16

SP - 1685

EP - 1692

JO - Tetrahedron: Assymmetry

JF - Tetrahedron: Assymmetry

IS - 9

ER -

Nitrite-mediated hydrolysis of epoxides catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1: A new tool for the kinetic resolution of epoxides

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