Enantioselective hydrolysis of unbranched aliphatic 1,2-epoxides by Rhodotorula glutinis

Epoxide hydrolase catalysed resolution of aliphatic terminal epoxides has been demonstrated for the hydrolysis of a homologous range of unbranched 1,2-epoxyalkanes by the yeast Rhodotorula glutinis. Both enantioselectivity and reaction rate were strongly influenced by the chain length of the epoxide used. Enantioselectivity showed an optimum in the hydrolysis of 1,2-epoxyhexane (E=84), Resolution of (+/-)-1,2-epoxyhexane resulted in (S)-1,2-epoxyhexane (e.e.>98%, yield=48%) and (R)-1,2-hexanediol (e.e.=83%, yield=47%). (C) 1998 Elsevier Science Ltd. All rights reserved.