Enantioconvergent production of (R)-1-phenyl-1,2-ethanediol from styrene oxide by combining the Solanum tuberosum and an evolved Agrobacterium radiobacter AD1 epoxide hydrolases.
Soluble epoxide hydrolase (EH) from the potato Solanum tuberosum and an evolved EH of the bacterium Agrobacterium radiobacter AD1, EchA-I219F, were purified for the enantioconvergent hydrolysis of racemic styrene oxide into the single product (R)-1-phenyl-1,2-ethanediol, which is an important intermediate for pharmaceuticals. EchA-I219F has enhanced enantioselectivity (enantiomeric ratio of 91 based on products) for converting (R)-styrene oxide to (R)-1-phenyl-1,2-ethanediol (2.0 +/- 0.2 micromol/min/mg), and the potato EH converts (S)-styrene oxide primarily to the same enantiomer, (R)-1-phenyl-1,2-ethanediol (22 +/- 1 micromol/min/mg), with an enantiomeric ratio of 40 +/- 17 (based on substrates). By mixing these two purified enzymes, inexpensive racemic styrene oxide (5 mM) was converted at 100% yield to 98% enantiomeric excess (R)-1-phenyl-1,2-ethanediol at 4.7 +/- 0.7 micromol/min/mg. Hence, at least 99% of substrate is converted into a single stereospecific product at a rapid rate.
Cao
Li
L
Department of Chemical Engineering, University of Connecticut, Storrs, Connecticut 06269-3222, USA.
Lee
Jintae
J
Chen
Wilfred
W
Wood
Thomas K
TK
D016960:Agrobacterium tumefaciens / Q000737:chemistry / Q000201:enzymology* / Q000235:genetics; D019943:Amino Acid Substitution; D001426:Bacterial Proteins / Q000737:chemistry* / Q000235:genetics; D004851:Epoxide Hydrolases / Q000737:chemistry* / Q000235:genetics; D004852:Epoxy Compounds / Q000737:chemistry; D005026:Ethylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D010940:Plant Proteins / Q000737:chemistry* / Q000235:genetics; D011198:Solanum tuberosum / Q000737:chemistry / Q000201:enzymology* / Q000235:genetics; D013237:Stereoisomerism; D013379:Substrate Specificity
D001426:Bacterial Proteins; D004852:Epoxy Compounds; D005026:Ethylene Glycols; D010940:Plant Proteins; C031474:styrene glycol; C013690:styrene oxide; D004851:Epoxide Hydrolases