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

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

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1437-1441
Number of pages5
JournalChemBioChem
Volume17
Issue number15
DOIs
Publication statusPublished - 3-Aug-2016

Keywords

  • biocatalysis
  • enantioselectivity
  • haloalkane dehalogenase
  • hydrolysis
  • LinB
  • regioselectivity
  • SPHINGOMONAS-PAUCIMOBILIS UT26
  • XANTHOBACTER-AUTOTROPHICUS GJ10
  • BIOTECHNOLOGICAL APPLICATIONS
  • GAMMA-HEXACHLOROCYCLOHEXANE
  • BRADYRHIZOBIUM-JAPONICUM
  • KINETIC RESOLUTION
  • PURIFICATION
  • DEGRADATION
  • SPECIFICITY
  • BACTERIUM

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