Highly enantioselective hydrolysis of alicyclic meso-epoxides with a bacterial epoxide hydrolase from Sphingomonas sp. HXN-200: simple syntheses of alicyclic vicinal trans-diols.
Hydrolysis of N-benzyloxycarbonyl-3,4-epoxy-pyrrolidine and cyclohexene oxide with the epoxide hydrolase of Sphingomonas sp. HXN-200, respectively, gave the corresponding vicinal trans-diols in high ee and yield, representing the first example of enantioselective hydrolysis of a meso-epoxide with a bacterial epoxide hydrolase.
Institute of Biotechnology, Swiss Federal Institute of Technology Zurich, ETH-Hoenggerberg, CH-8093 Zurich, Switzerland.
Dongliang
D
Chang
Zunsheng
Z
Wang
Maarten F
MF
Heringa
Renato
R
Wirthner
Bernard
B
Witholt
Zhi
Z
Li
D000438:Alcohols / Q000138:chemical synthesis*; D003510:Cyclohexanes / Q000737:chemistry; D053138:Cyclohexenes; D004851:Epoxide Hydrolases / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D006840:Hydrocarbons, Alicyclic / Q000737:chemistry*; D006868:Hydrolysis; D011759:Pyrrolidines / Q000737:chemistry; D020578:Sphingomonas / Q000201:enzymology*; D013237:Stereoisomerism
D000438:Alcohols; D003510:Cyclohexanes; D053138:Cyclohexenes; D004852:Epoxy Compounds; D006840:Hydrocarbons, Alicyclic; D011759:Pyrrolidines; C007193:cyclohexene oxide; D004851:Epoxide Hydrolases; C032519:pyrrolidine