The warfarin derivative brodifacoum and several closely related compounds are potent anticoagulant vitamin-K epoxide reductase inhibitors used widely as the active ingredient in many commercial rodenticide bait products. Technical brodifacoum is synthesized as a mixture of two diastereomers in varying proportion, and is incorporated in products as such. This characteristic can be measured and exploited for attribution and sample matching of technical brodifacoum, products containing it, or even material isolated from a biological matrix or from the environment. However, as diastereomers, their structure, properties, and reactivity both in vivo and ex vivo may differ from one other, and thereby could impact measurements of the diastereomer ratio. To address this possibility, NMR spectroscopy was used to characterize the conformation, dynamics, and ex vivo degradation of the two brodifacoum diastereomers in several media and solvent conditions, revealing significant differences between them that are driven by the configurations at the stereocenters in each diastereomer.

Stereochemical influence on the conformation, dynamics, and reactivity of the two diastereomers of brodifacoum

248th National Meeting (2014)

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