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Issue 26, 2012
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Catalytic activity of halohydrin dehalogenases towards spiroepoxides

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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

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Publication details

The article was received on 03 Mar 2012, accepted on 24 Apr 2012 and first published on 25 Apr 2012


Article type: Paper
DOI: 10.1039/C2OB25470K
Citation: Org. Biomol. Chem., 2012,10, 5063-5072
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    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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