Issue 26, 2012
From the journal:

Organic & Biomolecular Chemistry

Catalytic activity of halohydrin dehalogenases towards spiroepoxides†

Maja Majerić Elenkov,*a   Ines Primožič,b   Tomica Hrenar,b   Ana Smolko,a   Irena Dokli,a   Branka Salopek-Sondia  and  Lixia Tangc  

* Corresponding authors

a Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia
E-mail: majeric@irb.hr
Fax: +385 1 4680-108
Tel: +3851 4560965

b Faculty of Science, University of Zagreb, Zagreb, Croatia
E-mail: ines.primozic@chem.pmf.hr
Fax: +3851 4606 401
Tel: +385 1 4606 400

c University of Electronic Science and Technology, No.4, Section 2, North Jianshe Road, Chengdu, China
E-mail: lixiatang@uestc.edu.cn
Fax: +8628 83208238
Tel: +86 28 83208232

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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Article information

DOI
https://doi.org/10.1039/C2OB25470K
Article type
Paper
Submitted
03 Mar 2012
Accepted
24 Apr 2012
First published
25 Apr 2012

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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