Asymmetric epoxidation of styrene derivatives by styrene monooxygenase from Pseudomonas sp. LQ26: effects of α- and β-substituents

Recombinant Escherichia coli expressing a styrene monooxygenase, StyAB2, from Pseudomonas sp. LQ26 was applied to synthesize a range of chiral epoxides from conjugated styrene derivatives with excellent (>99%) enantioselectivity in most cases. The substrate preference was studied with a special focus on the steric effect of α- and β-substituents.

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(S)-Styrene oxideC8H8OEe >99%[α]D25=+32.1 (c 1.02, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)

(2S,3S)-2-Methyl-3-phenyloxiraneC9H10OEe >99%[α]D25=-41.8 (c 1.00, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (2S,3S)

(S)-2-Methyl-2-phenyloxiraneC9H10OEe >99%[α]D25=+16 (c 0.20, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)

(S)-2,2-Dimethyl-3-phenyloxiraneC10H12OEe >99%[α]D25=-23.6 (c 0.85, benzene)Source of chirality: enzymatic catalysisAbsolute configuration: (S)

(2S,3S)-2-Phenyl-3-vinyloxiraneC10H10OEe 96%[α]D25=-42.3 (c 0.35, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (2S,3S)

(S)-2-Ethyl-2-phenyloxiraneC10H12OEe >99%[α]D25=+23.1 (c 0.34, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)

(2S,3S)-2-Isopropyl-3-phenyloxiraneC11H14OEe >99%[α]D25=-62.4 (c 0.25, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (2S,3S)

(S)-2-Phenyl-2-propyloxiraneC11H14OEe >99%[α]D25=+32.3 (c 0.26, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)

(2S,3S)-3-Phenyloxiran-2-yl methanolC9H10O2Ee >99%[α]D25=-48 (c 0.3, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (2S,3S)

(1S,2S)-1-Phenylcyclohexene oxideC12H14OEe 65%[α]D25=-30.9 (c 1.01, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (1S,2S)

(S)-2-(Naphthalen-2-yl)oxiraneC12H10OEe >99%[α]D25=+17 (c 0.72, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)

(S)-4-(Oxiran-2-yl)-2, 3-dihydrobenzofuranC10H10O2Ee >99%[α]D25=+40.8 (c 1.0, CHCl3)Source of chirality: enzymatic catalysisAbsolute configuration: (S)