Issue 26, 2012

Catalytic activity of halohydrin dehalogenases towards spiroepoxides

Abstract

A novel activity of halohydrin dehalogenases towards spiroepoxides has been found. The enzyme from Arthrobacter sp. (HheA) catalysed highly regioselective azidolysis of spiroepoxides containing 5, 6 and 7-membered cycloalkane rings, while the enzyme from Agrobacterium radiobacter (HheC), besides high regioselectivity, also displayed moderate to high enantioselectivity (E up to >200) that can be applied for the kinetic resolution of chiral spiroepoxides. The orientations of spiroepoxides in the active site of halohydrin dehalogenases were studied by quantum-chemical calculations and docking simulations. Analyses of the complexes obtained revealed the origins of diastereoselectivity and enantioselectivity of the investigated biotransformations.

Graphical abstract: Catalytic activity of halohydrin dehalogenases towards spiroepoxides

Supplementary files

Article information

Article type
Paper
Submitted
03 Mar 2012
Accepted
24 Apr 2012
First published
25 Apr 2012

Org. Biomol. Chem., 2012,10, 5063-5072

Catalytic activity of halohydrin dehalogenases towards spiroepoxides

M. Majerić Elenkov, I. Primožič, T. Hrenar, A. Smolko, I. Dokli, B. Salopek-Sondi and L. Tang, Org. Biomol. Chem., 2012, 10, 5063 DOI: 10.1039/C2OB25470K

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