Biosynthesis of (R)-phenyl-1,2-ethanediol from racemic styrene oxide by using bacterial and marine fish epoxide hydrolases.
Enantio-convergent hydrolysis of racemic styrene oxides was achieved to prepare enantiopure (R)-phenyl-1,2-ethanediol by using two recombinant epoxide hydrolases (EHs) of a bacterium, Caulobacter crescentus, and a marine fish, Mugil cephalus. The recombinant C. crescentus EH primarily attacked the benzylic carbon of (S)-styrene oxide, while the M. cephalus EH preferentially attacked the terminal carbon of (R)-styrene oxide, thus leading to the formation of (R)-phenyl-1,2-ethanediol as the main product. (R)-Phenyl-1,2-ethanediol was obtained with 90% enantiomeric excess and yield as high as 94% from 50 mM racemic styrene oxides in a one-pot process.
Kim
Hee Sook
HS
Department of Food Science and Biotechnology, Kyungsung University, Busan 608-736, Korea.
Lee
Ok Kyung
OK
Hwang
Seungha
S
Kim
Beum Jun
BJ
Lee
Eun Yeol
EY
D000818:Animals; D016935:Caulobacter crescentus / Q000201:enzymology* / Q000235:genetics*; D004852:Epoxy Compounds / Q000737:chemistry*; D005026:Ethylene Glycols / Q000138:chemical synthesis*; D005399:Fishes / Q000378:metabolism*; D006867:Hydrolases / Q000737:chemistry*; D008386:Marine Biology; D011994:Recombinant Proteins / Q000737:chemistry
D004852:Epoxy Compounds; D005026:Ethylene Glycols; D011994:Recombinant Proteins; C031474:styrene glycol; C013690:styrene oxide; D006867:Hydrolases