Chiral organophosphorus compounds are usually used as insecticides in their racemic form. However, enantiomers are known to interact stereospecifically with biological systems and in many cases the exposure to the racemic mixture leads to selective microbial degradation of one of the two enantiomers. Moreover, the two enantiomers may degrade or accumulate in the environment differently, or may be toxic in different ways toward other species. Enantiomers of three different racemic organophosphate compounds were isolated by HPLC chromatography (acephate, isophenphos and ruelene). Their absolute configuration was determined through the concerted use of three different spectroscopic techniques: optical rotatory dispersion (ORD), electronic circular dichroism (ECD), vibrational circular dichroim (VCD). To arrive to the definitive stereochemical assignment of the derivatives we have considered both experimental and TD-DFT predicted ORD, ECD and VCD responses. For all compounds we have investigate the biological activities of the racemic mixture and of the single enantiomers through ND50 (neurotoxicity) and enzymatic activity on EE-AChE studies.

Chiroptical characterization and biological evaluation of selected organophosphates

247th National Meeting (2014)

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