Chiral Epoxides, their Enantioselective Reactivity Towards Nucleic Acids, and a First Outline of a Quantum Chemical Structure-Reactivity Calculation
Liver microsomes of mice, rats and humans metabolize prochiral vinyl precursors to chiral epoxides with different ratios for the two enantiomers (Wistuba et al. 1989), which may interact in different ways with chiral structures in the cell. Thus, the pharmacological effects of chiral pharmaceutics (L-Dopa, D-Penicillamine) are known to depend on the configuration of the molecule. A similar enantioselectivity may therefore modulate genotoxicity of metabolically formed chiral epoxides when they react with chiral (in terms of their conformation) macromolecular nucleic acids.
KeywordsCircular Dichroism Spectrum Propylene Oxide Equilibrium Dialysis Styrene Oxide Pure Enantiomer
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