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It was confirmed that the enantiomers in racemic S-2571 (O-ethyl O-2-nitro5-methylphenyl N-isopropyl phosphoramidothioate) were stereoselectively metabolized by rabbit liver microsomal mixed function oxidase to give dextrorotatory products of parent compound, the oxon analog and derivatives hydroxylated at the 5-methyl group. The corresponding products obtained from (+)-S-2571 were all dextrorotatory and those from (-)-S-2571 were levorotatory. Oxidation of the optical isomers of S-2571 to the corresponding oxon analogs by UV light was also stereospecific. Comparison with the results from m-chloroperoxybenzoic acidd oxidation suggests that oxidation of P=S to P=0 by the mixed function oxidase and UV light may proceed with retention of configuration at phosphorus.

nippon nōyaku gakkaishi

Stereospecificity in Oxidation of the Optical Isomers of &lt;i&gt;O&lt;/i&gt;-Ethyl &lt;i&gt;O&lt;/i&gt;-2-Nitro-5-Methylphenyl &lt;i&gt;N&lt;/i&gt;-Isopropyl Phosphoramidothioate (S-2571) by Liver Mixed Function Oxidase and UV Light