Oxidations catalyzed by phenylacetone monooxygenase from Thermobifida fusca

Several organic sulfides, ketones and other organic systems have been tested as substrates in oxidation reactions catalyzed by the recently discovered phenylacetone monooxygenase from Thermobifida fusca. The biocatalytic properties of this Baeyer–Villiger monooxygenase have been studied, revealing reactivity with a large range of sulfides and ketones. Oxidations of several sulfoxides, an amine and an organoboron compound were also observed. The enzyme is able to oxidize a number of sulfides with excellent enantioselectivity, demonstrating the catalytic potential of this novel biocatalyst.

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(S)-Phenyl propyl sulfoxideC9H12OSEe = 21% (HPLC, Chiralcel OB)[α]D25=-51.8 (c 1.16, CHCl3)Source of chirality: enzymatic oxidationAbsolute configuration: S

(S)-Cyclopropyl phenyl sulfoxideC9H10OSEe = 48% (HPLC, Chiralcel OD)[α]D25=+56.6 (c 0.71, acetone)Source of chirality: enzymatic oxidationAbsolute configuration: S

(R)-Methyl p-nitrophenyl sulfoxideC7H7NO3SEe = 76% (HPLC, Chiralcel OB)[α]D25=+84.1 (c 1.30 CHCl3)Source of chirality: enzymatic oxidationAbsolute configuration: R

(S)-Benzyl isopropyl sulfoxideC10H12OSEe = 41% (HPLC, Chiralcel OD)[α]D25=+53.7 (c 1.29, EtOH)Source of chirality: enzymatic oxidationAbsolute configuration: