Naslov
Catalytic activity of halohydrin dehalogenases towards spiroepoxides

Autori
Maja Majerić Elenkov ; Ines Primožič ; Tomica Hrenar ; Ana Smolko ; Irena Dokli ; Branka Salopek-Sondi ; Lixia Tang

Izvornik
Organic & biomolecular chemistry (1477-0520) 10 (2012); 5063-5072

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
halohydrin dehalogenases ; spiroepoxides ; regioselectivity ; enantioselectivity ; diastereoselectivity

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA