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 language | English |
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Pages (from-to) | 1437-1441 |
Number of pages | 5 |
Journal | ChemBioChem |
Volume | 17 |
Issue number | 15 |
DOIs | |
Publication status | Published - 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