Enantiotopic Demethylation of Fenitrothion into Partially Racemized (<i>R</i>)<sub>p</sub>-(+)-Desmethylfenitrothion by Mouse Liver Homogenate and Mice

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  • フェニトロチオンのマウス肝臓ホモジネートおよびマウスによる (<i>R</i>)<sub>p</sub>-(+)-デスメチルフェニトロチオンへのエナンチオトピック脱メチル化反応
  • フェニトロチオンのマウス肝臓ホモジネートおよびマウスによる(R)p-(+)-デスメチルフェニトロチオンへのエナンチオトピック脱メチル化反応〔英文〕(短報)
  • フェニトロチオン ノ マウス カンゾウ ホモジネート オヨビ マウス ニ ヨル(R)p-(+)-デスメチルフェニトロチオン エ ノ エナンチオトピック ダツメチルカ ハンノウ 〔 エイブン 〕(タンポウ)

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Abstract

Metabolic experiments of fenitrothion with mouse liver homogenate and mice were conducted, in order to examine whether an enantiotopic demethylation reaction occurs or not during the metabolism. Metabolic desmethylfenitrothion extracted was chemically derivatized into the diastereomeric phosphoramidothioate with (S)-(-)-α-phenylethylamine, which was analyzed by HPLC to determine their diastereomeric composition. The results showed that a larger amount of (R)p-(+)-desmethylfenitrothion was produced with a lesser amount of a (S)p-(-) enantiomer in both in vitro and in vivo metabolism, whose absolute stereochemistry was determined by comparative analysis of 1H-NMR spectra of the diastereomers.

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