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. |
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@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.
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