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

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.

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

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10600 1.6 Biological sciences
• Country of publisher: Germany
• Confidentiality degree: is not subject to a state or trade secret
• WWW: 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
• Tags: AKR, rivok
• Tags: International impact, Reviewed

Abstract

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