title: 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.
authors.affiliation: Ruđer Bošković Institute, Bijenička c. 54, 10000 Zagreb, Croatia. majeric@irb.hr
authors.forename: Maja
authors.initials: M
authors.lastname: Majerić Elenkov
authors.forename: Ines
authors.initials: I
authors.lastname: Primožič
authors.forename: Tomica
authors.initials: T
authors.lastname: Hrenar
authors.forename: Ana
authors.initials: A
authors.lastname: Smolko
authors.forename: Irena
authors.initials: I
authors.lastname: Dokli
authors.forename: Branka
authors.initials: B
authors.lastname: Salopek-Sondi
authors.forename: Lixia
authors.initials: L
authors.lastname: Tang
mesh_terms: D060054:Agrobacterium / Q000201:enzymology; D001173:Arthrobacter / Q000737:chemistry / Q000201:enzymology*; D001386:Azides / Q000378:metabolism; D020134:Catalytic Domain; D004852:Epoxy Compounds / Q000378:metabolism*; D006867:Hydrolases / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D013141:Spiro Compounds / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001386:Azides; D004852:Epoxy Compounds; D013141:Spiro Compounds; D006867:Hydrolases; C430848:halohydrin dehalogenase