Regio- and Enantioselective Sequential Dehalogenation of
rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB

J 2016

Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB

GROSS, J., Zbyněk PROKOP, D. JANSSEN, Kurt FABER, M. HALL et. al.

Basic information

Original name

Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB

Authors

GROSS, J. (40 Austria), Zbyněk PROKOP (203 Czech Republic, guarantor, belonging to the institution), D. JANSSEN (528 Netherlands), Kurt FABER (40 Austria) and M. HALL (40 Austria)

Edition

CHEMBIOCHEM, WILEY-V C H VERLAG GMBH, 2016, 1439-4227

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10600 1.6 Biological sciences

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 2.847

RIV identification code

RIV/00216224:14310/16:00088568

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.1002/cbic.201600227

UT WoS

000383586300010

Keywords in English

biocatalysis; enantioselectivity; haloalkane dehalogenase; hydrolysis; LinB; regioselectivity

Abstract

V originále

The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by haloalkane dehalogenase LinB fromSphingobium japonicum UT26 proceeds in a sequential fashion via initial formation of intermediate haloalcohols followed by a second hydrolytic step to produce the final diol. Detailed investigation of the course of the reaction revealed favored nucleophilic displacement of the sec-halogen in the first hydrolytic event with pronounced (R)-enantioselectivity. The second hydrolysis step proceeded with a regioselectivity switch at the primary position with preference for the (S)-enantiomer. Due to complex competition between all eight possible pathways, intermediate haloalcohols could be formed with moderate to good ee values [(S)-4-bromobutan-2-ol in up to 87% ee]. Similarly, (S)-1,3-butanediol was formed in max. ee 35% before full hydrolysis furnished the racemic diol product.

Links

ED2.1.00/19.0382, research and development project

Name: CETOCOEN UPgrade

GA16-07965S, research and development project

Name: Řízená evoluce dynamických elementů v enzymech s využitím mikrofluidních čipů

Investor: Czech Science Foundation

LO1214, research and development project

Name: Centrum pro výzkum toxických látek v prostředí (Acronym: RECETOX)

Investor: Ministry of Education, Youth and Sports of the CR

Citovat

GROSS, J., Zbyněk PROKOP, D. JANSSEN, Kurt FABER and M. HALL. Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB. CHEMBIOCHEM. WILEY-V C H VERLAG GMBH, 2016, vol. 17, No 15, p. 1437-1441. ISSN 1439-4227. Available from: https://dx.doi.org/10.1002/cbic.201600227.

@article{1368405,
   author = {Gross, J. and Prokop, Zbyněk and Janssen, D. and Faber, Kurt and Hall, M.},
   article_number = {15},
   doi = {http://dx.doi.org/10.1002/cbic.201600227},
   keywords = {biocatalysis; enantioselectivity; haloalkane dehalogenase; hydrolysis; LinB; regioselectivity},
   language = {eng},
   issn = {1439-4227},
   journal = {CHEMBIOCHEM},
   title = {Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB},
   url = {http://dx.doi.org/10.1002/cbic.201600227},
   volume = {17},
   year = {2016}
}

TY  - JOUR
ID  - 1368405
AU  - Gross, J. - Prokop, Zbyněk - Janssen, D. - Faber, Kurt - Hall, M.
PY  - 2016
TI  - Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB
JF  - CHEMBIOCHEM
VL  - 17
IS  - 15
SP  - 1437-1441
EP  - 1437-1441
PB  - WILEY-V C H VERLAG GMBH
SN  - 14394227
KW  - biocatalysis
KW  - enantioselectivity
KW  - haloalkane dehalogenase
KW  - hydrolysis
KW  - LinB
KW  - regioselectivity
UR  - http://dx.doi.org/10.1002/cbic.201600227
L2  - http://dx.doi.org/10.1002/cbic.201600227
N2  - The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by haloalkane dehalogenase LinB fromSphingobium japonicum UT26 proceeds in a sequential fashion via initial formation of intermediate haloalcohols followed by a second hydrolytic step to produce the final diol. Detailed investigation of the course of the reaction revealed favored nucleophilic displacement of the sec-halogen in the first hydrolytic event with pronounced (R)-enantioselectivity. The second hydrolysis step proceeded with a regioselectivity switch at the primary position with preference for the (S)-enantiomer. Due to complex competition between all eight possible pathways, intermediate haloalcohols could be formed with moderate to good ee values [(S)-4-bromobutan-2-ol in up to 87% ee]. Similarly, (S)-1,3-butanediol was formed in max. ee 35% before full hydrolysis furnished the racemic diol product.
ER  -

GROSS, J., Zbyněk PROKOP, D. JANSSEN, Kurt FABER and M. HALL. Regio- and Enantioselective Sequential Dehalogenation of rac-1,3-Dibromobutane by Haloalkane Dehalogenase LinB. \textit{CHEMBIOCHEM}. WILEY-V C H VERLAG GMBH, 2016, vol.~17, No~15, p.~1437-1441. ISSN~1439-4227. Available from: https://dx.doi.org/10.1002/cbic.201600227.

Detailed Information on Publication Record