Naslov
Enantioselective Ring Opening of Epoxides with Cyanide Catalysed by Halohydrin Dehalogenase: A New Approach to Non-Racemic b-Hydroxy Nitriles

Autori
Majerić Elenkov, Maja ; Hauer, Bernhard ; Janssen, Dick

Izvornik
Advanced Synthesis & Catalysis (1615-4150) 348 (2006); 579-585

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

Ključne riječi
cyanide; epoxides; halohydrin dehalogenase; kinetic resolution

Sažetak
Halohydrin dehalogenases (HheA, HheB and HheC) were found to efficiently catalyse a carbon-carbon bond forming reaction between terminal aliphatic epoxides and cyanide, yielding b-hydroxynitriles. With all three enzymes nucleophilic ring opening of epoxides proceeds with high regioselectivity to the b-carbon atom. Activity, enantioselectivity and enantiopreference depend on the type of enzyme and the substrate structure. HheC was found to be the most selective among the tested enzymes. The enantioselectivity toward monosubstituted epoxides varies from moderate to high (E = 5-106), while resolution of 2, 2-disubstituted epoxides proceeds with very high enantioselectivity (E = 141 and 200). The results show that halohydrin dehalogenases may become attractive catalysts for the facile preparation of enantiopure b-hydroxynitriles from racemic epoxides.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA