Chiral organophosphorus compounds are usually used as insecticides in their racemic forms for economic reasons. 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.We have isolated the enantiomers of several chiral organophosphorus compounds and determined their absolute configuration through the concerted use of three different spectroscopic techniques such as 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 investigated the biological activities of the racemic mixture and of the single enantiomers through ND50 (neurotoxicity) and enzymatic activity on EE-AChE studies.

Chiral organophosphates: Separation, spectroscopic characterization, and biological evaluation

245th National Meeting (2013)

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