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

Johannes Gross, Zbynek Prokop, Dick Janssen, Kurt Faber, Melanie Hall*

*Bijbehorende auteur voor dit werk

OnderzoeksoutputAcademicpeer review

1 Citaat (Scopus)

Samenvatting

The hydrolytic dehalogenation of rac-1,3-dibromobutane catalyzed by the haloalkane dehalogenase LinB from Sphingobium japonicum UT26 proceeds in a sequential fashion: 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. Because of complex competition between all eight possible reactions, intermediate haloalcohols formed with moderate to good ee ((S)-4-bromo-butan-2-ol: up to 87%). Similarly, (S)-butane-1,3-diol was formed at a maximum ee of 35% before full hydrolysis furnished the racemic diol product.

Originele taal-2English
Pagina's (van-tot)1437-1441
Aantal pagina's5
TijdschriftChemBioChem
Volume17
Nummer van het tijdschrift15
DOI's
StatusPublished - 3-aug-2016

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