| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345855 | Tetrahedron: Asymmetry | 2012 | 8 Pages |
Herein we report the production of enantiopure epoxides through biocatalysis using recombinant Escherichia coli cells expressing Rhodococcus sp. ST-10 styrene monooxygenase (SMO) and Leifsonia sp. S749 alcohol dehydrogenase (LSADH) genes are described. Rhodococcus sp. ST-10 SMO catalyzed the epoxidation of various alkenes, including styrene derivatives, vinyl pyridines, and linear alkenes, to give (S)-epoxides. NADH was regenerated by the reduction of NAD+ by LSADH with 2-propanol. The E. coli biocatalyst was used in an aqueous/organic biphasic reaction system and the reaction conditions were optimized. Under the optimized conditions, 170 mM of (S)-styrene oxide was obtained from styrene in the organic phase with excellent enantiomeric excess (99.8%). This biocatalytic process was used to synthesize various (S)-epoxides.
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(S)-Styrene oxideC8H8OEe = 99.8%[α]D24.5=+25.1 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-2-Chlorostyrene oxideC8H7ClOEe >99.9%[α]D24.5=+65.6 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-3-Chlorostyrene oxideC8H7ClOEe >99.9%[α]D24.5=+9.5 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-4-Chlorostyrene oxideC8H7ClOEe = 97.5%[α]D24.5=+24.9 (c 1.06, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-2-Fluorostyrene oxideC8H7FOEe >99.9%[α]D24.5=+30.8 (c 1.08, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-4-Fluorostyrene oxideC8H7FOEe = 99.1%[α]D24.5=+16.3 (c 1.11, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (S)
(S)-2-Bromostyrene oxideC8H7BrOEe >99.9%[α]D24.5=+56.2 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (S)
(S)-4-Bromostyrene oxideC8H7BrOEe = 96.3%[α]D24.5=+14.6 (c 1.05, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-2-Methylstyrene oxideC9H10OEe = 62.8%[α]D24.5=+38.8 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-4-Methylstyrene oxideC9H10OEe = 93.9%[α]D24.5=+15.7 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(S)-α-Methylstyrene oxideC9H10OEe = 99.3%[α]D24.5=+21.3 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (S)
(1S,2S)-1-Phenylpropylene oxideC9H10OEe = 98.5%[α]D24.5=-54.5 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (1S,2S)
(2S,3S)-3-PhenylglycidolC9H10O2Ee >99.9%[α]D24.5=-58.7 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (2S,3S)
(S)-(2,3-Epoxypropyl)benzeneC9H10OEe = 64.2%[α]D24.5=-12.0 (c 1.00, EtOH)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
(1S,2R)-Indene oxideC9H8OEe = 99.8%[α]D23.2=+53.0 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (1S,2R)
(S)-2-OxyranylpyridineC7H7NOEe >99.9%[α]D24.5=+23.3 (c 0.53, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (S)
(S)-4-OxyranylpyridineC7H7NOEe > 99.9%[α]D24.5=+27.7 (c 0.50, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (S)
(S)-Methyl-p-tolyl sulfoxideC8H10OSEe = 54.5%[α]D23.7=-98.7 (c 0.50, EtOH)Source of chirality: styrene monooxygenase-catalyzed epooxidationAbsolute configuration: (S)
(S)-1,2-EpoxyhexaneC6H12OEe = 94.8%[α]D24.5=-9.1 (c 1.00, CHCl3)Source of chirality: styrene monooxygenase-catalyzed epoxidationAbsolute configuration: (S)
