Epoxide hydrolase-catalyzed enantioselective synthesis of chiral 1,2-diols via desymmetrization of meso-epoxides. lzhao@diversa.com.
The discovery, from nature, of a diverse set of microbial epoxide hydrolases is reported. The utility of a library of epoxide hydrolases in the synthesis of chiral 1,2-diols via desymmetrization of a wide range of meso-epoxides, including cyclic as well as acyclic alkyl- and aryl-substituted substrates, is demonstrated. The chiral (R,R)-diols were furnished with high ee's and yields. The discovery of the first microbial epoxide hydrolases providing access to complementary (S,S)-diols is also described.
Zhao
Lishan
L
Diversa Corporation, 4955 Directors Place, San Diego, California 92121, USA. lzhao@diversa.com
Han
Bin
B
Huang
Zilin
Z
Miller
Mark
M
Huang
Hongjun
H
Malashock
Dan S
DS
Zhu
Zuolin
Z
Milan
Aileen
A
Robertson
Dan E
DE
Weiner
David P
DP
Burk
Mark J
MJ
D000438:Alcohols / Q000737:chemistry*; D002384:Catalysis; D004851:Epoxide Hydrolases / Q000737:chemistry* / Q000378:metabolism; D004852:Epoxy Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D000438:Alcohols; D004852:Epoxy Compounds; D004851:Epoxide Hydrolases