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

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Authors

GROSS J. PROKOP Zbyněk JANSSEN D. FABER Kurt HALL M.

Year of publication 2016
Type Article in Periodical
Magazine / Source CHEMBIOCHEM
MU Faculty or unit

Faculty of Science

Citation
Web http://dx.doi.org/10.1002/cbic.201600227
Doi http://dx.doi.org/10.1002/cbic.201600227
Field Biochemistry
Keywords biocatalysis; enantioselectivity; haloalkane dehalogenase; hydrolysis; LinB; regioselectivity
Description 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.
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