Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides

Maja Majeric Elenkov; Lixia Tang; Auke Meetsma; Bernhard Hauer; Dick B. Janssen

doi:10.1021/ol800698t

Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides

Maja Majeric Elenkov
, Lixia Tang
, Auke Meetsma
, Bernhard Hauer
, Dick B. Janssen^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

85 Citations (Scopus)

830 Downloads (Pure)

Abstract

Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxazolidinones.

Original language	English
Pages (from-to)	2417-2420
Number of pages	4
Journal	Organic letters
Volume	10
Issue number	12
DOIs	https://doi.org/10.1021/ol800698t
Publication status	Published - 19-Jun-2008

Keywords

HALOHYDRIN DEHALOGENASES
HYDROLASES
REAGENTS
ALCOHOLS

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CCDC 680924: Experimental Crystal Structure Determination
Majeric Elenkov, M. (Contributor), Tang, L. (Contributor), Meetsma, A. (Contributor), Hauer, B. (Contributor) & Janssen, D. B. (Contributor), University of Groningen, 11-Mar-2008
DOI: 10.5517/ccqvk9d
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title = "Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides",

abstract = "Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98\% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxazolidinones.",

keywords = "HALOHYDRIN DEHALOGENASES, HYDROLASES, REAGENTS, ALCOHOLS",

author = "\{Majeric Elenkov\}, Maja and Lixia Tang and Auke Meetsma and Bernhard Hauer and Janssen, \{Dick B.\}",

year = "2008",

month = jun,

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doi = "10.1021/ol800698t",

language = "English",

volume = "10",

pages = "2417--2420",

journal = "Organic letters",

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T1 - Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides

AU - Majeric Elenkov, Maja

AU - Tang, Lixia

AU - Meetsma, Auke

AU - Hauer, Bernhard

AU - Janssen, Dick B.

PY - 2008/6/19

Y1 - 2008/6/19

N2 - Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxazolidinones.

AB - Halohydrin dehalogenase from Agrobacterium radiobacter catalyzed the enantioselective ring opening of terminal epoxides with cyanate as a nucleophile, yielding 5-substituted oxazolidinones in high yields and with high enantiopurity (69-98% ee). This is the first example of the biocatalytic conversion of a range of epoxides to the corresponding oxazolidinones.

KW - HALOHYDRIN DEHALOGENASES

KW - HYDROLASES

KW - REAGENTS

KW - ALCOHOLS

U2 - 10.1021/ol800698t

DO - 10.1021/ol800698t

M3 - Article

SN - 1523-7060

VL - 10

SP - 2417

EP - 2420

JO - Organic letters

JF - Organic letters

IS - 12

ER -

Formation of enantiopure 5-substituted oxazolidinones through enzyme-catalysed kinetic resolution of epoxides

Abstract

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CCDC 680924: Experimental Crystal Structure Determination

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