Dynamic kinetic resolution process employing haloalkane dehalogenase

Alja Westerbeek; Wiktor Szymanski; Ben L. Feringa; Dick B. Janssen

doi:10.1021/cs2003565

Dynamic kinetic resolution process employing haloalkane dehalogenase

Alja Westerbeek
, Wiktor Szymanski
, Ben L. Feringa
, Dick B. Janssen^*

^*Corresponding author for this work

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

19 Citations (Scopus)

41 Downloads (Pure)

Abstract

The first dynamic kinetic resolution process with a haloalkane dehalogenase is described, allowing the efficient preparation of enantiopure alpha-hydroxyarnides from racemic alpha-bromoamides. A simple Membrane reactor is used to separate the enzyme from the nonsoluble, polymer based, and metal-free racemizing agent. A model substrate, N-pheny1-2-bromopropionamide, was converted to (S)-N-phenyl-2-hydroxypropionamide either with 63% yield and 95% e.e or with 78% yield and 88% e.e.

Original language	English
Pages (from-to)	1654-1660
Number of pages	7
Journal	ACS Catalysis
Volume	1
Issue number	12
DOIs	https://doi.org/10.1021/cs2003565
Publication status	Published - Dec-2011

Keywords

dynamic kinetic resolution
enantioselective biocatalysis
haloalkane dehalogenases
alpha-hydroxyamides
racemization methods
CHEMOENZYMATIC SYNTHESIS
ALPHA-HYDROXYAMIDES
RACEMIZATION
RUTHENIUM
ALCOHOLS
ENZYME
ENANTIOSELECTIVITY
HYDROGENATION
COMPLEX
KETONES

Access to Document

10.1021/cs2003565

Handle.net

Persistent link

Embargoed Document

2011ACSCatalWesterbeek.pdf
Final publisher's version, 1.11 MB
Request copy

Cite this

@article{07471e1c9b1f4d85a0f8b0ab10f4ca60,

title = "Dynamic kinetic resolution process employing haloalkane dehalogenase",

abstract = "The first dynamic kinetic resolution process with a haloalkane dehalogenase is described, allowing the efficient preparation of enantiopure alpha-hydroxyarnides from racemic alpha-bromoamides. A simple Membrane reactor is used to separate the enzyme from the nonsoluble, polymer based, and metal-free racemizing agent. A model substrate, N-pheny1-2-bromopropionamide, was converted to (S)-N-phenyl-2-hydroxypropionamide either with 63\% yield and 95\% e.e or with 78\% yield and 88\% e.e.",

keywords = "dynamic kinetic resolution, enantioselective biocatalysis, haloalkane dehalogenases, alpha-hydroxyamides, racemization methods, CHEMOENZYMATIC SYNTHESIS, ALPHA-HYDROXYAMIDES, RACEMIZATION, RUTHENIUM, ALCOHOLS, ENZYME, ENANTIOSELECTIVITY, HYDROGENATION, COMPLEX, KETONES",

author = "Alja Westerbeek and Wiktor Szymanski and Feringa, \{Ben L.\} and Janssen, \{Dick B.\}",

note = "Relation: http://www.rug.nl/research/stratingh/ date\_submitted:2011 Rights: University of Groningen, Stratingh Institute for Chemistry",

year = "2011",

month = dec,

doi = "10.1021/cs2003565",

language = "English",

volume = "1",

pages = "1654--1660",

journal = "ACS Catalysis",

publisher = "AMER CHEMICAL SOC",

number = "12",

}

TY - JOUR

T1 - Dynamic kinetic resolution process employing haloalkane dehalogenase

AU - Westerbeek, Alja

AU - Szymanski, Wiktor

AU - Feringa, Ben L.

AU - Janssen, Dick B.

N1 - Relation: http://www.rug.nl/research/stratingh/ date_submitted:2011 Rights: University of Groningen, Stratingh Institute for Chemistry

PY - 2011/12

Y1 - 2011/12

N2 - The first dynamic kinetic resolution process with a haloalkane dehalogenase is described, allowing the efficient preparation of enantiopure alpha-hydroxyarnides from racemic alpha-bromoamides. A simple Membrane reactor is used to separate the enzyme from the nonsoluble, polymer based, and metal-free racemizing agent. A model substrate, N-pheny1-2-bromopropionamide, was converted to (S)-N-phenyl-2-hydroxypropionamide either with 63% yield and 95% e.e or with 78% yield and 88% e.e.

AB - The first dynamic kinetic resolution process with a haloalkane dehalogenase is described, allowing the efficient preparation of enantiopure alpha-hydroxyarnides from racemic alpha-bromoamides. A simple Membrane reactor is used to separate the enzyme from the nonsoluble, polymer based, and metal-free racemizing agent. A model substrate, N-pheny1-2-bromopropionamide, was converted to (S)-N-phenyl-2-hydroxypropionamide either with 63% yield and 95% e.e or with 78% yield and 88% e.e.

KW - dynamic kinetic resolution

KW - enantioselective biocatalysis

KW - haloalkane dehalogenases

KW - alpha-hydroxyamides

KW - racemization methods

KW - CHEMOENZYMATIC SYNTHESIS

KW - ALPHA-HYDROXYAMIDES

KW - RACEMIZATION

KW - RUTHENIUM

KW - ALCOHOLS

KW - ENZYME

KW - ENANTIOSELECTIVITY

KW - HYDROGENATION

KW - COMPLEX

KW - KETONES

U2 - 10.1021/cs2003565

DO - 10.1021/cs2003565

M3 - Article

VL - 1

SP - 1654

EP - 1660

JO - ACS Catalysis

JF - ACS Catalysis

IS - 12

ER -

Dynamic kinetic resolution process employing haloalkane dehalogenase

Abstract

Keywords

Access to Document

Handle.net

Embargoed Document

Fingerprint

Cite this