Catalytic activity of halohydrin dehalogenases towards spiroepoxides (CROSBI ID 183633)
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Maja Majerić Elenkov ; Ines Primožič ; Tomica Hrenar ; Ana Smolko ; Irena Dokli ; Branka Salopek-Sondi ; Lixia Tang
engleski
Catalytic activity of halohydrin dehalogenases towards spiroepoxides
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, displayed also 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.
halohydrin dehalogenases ; spiroepoxides ; regioselectivity ; enantioselectivity ; diastereoselectivity
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