We learn at degree level that the enantiomeric compounds have properties which are exactly the same, but for measurements like polarised light. However, when enantiomers are measured in common assays used in drug hunting, what effects to we see, and by how much do they vary? In this #BucketListPapers, Leach et al looked at enantiomeric matched pairs and found that, for the likes of aqueous solubility, that there was no difference, as expected, but for some measured properties, like Cytochrome P450 inhibition there were significant differences. Perhaps most surprisingly were the absorption measurements, these showed no difference for both A-B, and for efflux ratio.
Enantiomeric pairs reveal that key medicinal chemistry parameters vary more than simple physical property based models can explain.
Med. Chem. Commun., 2012, 3, 528
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