Resolving Agents – Achiral? Chiral?

A great question came my way right after lecture: can resolving agents by achiral?

The short answer is no.
To explain my “no” answer, imagine that “mint receptor protein” is achiral. In this case, R-M (the complex of R-carvone and mint receptor protein) would be the mirror image of S-M. The complexes would be enantiomers and they would have identical energies.

This means that ΔG would be identical for the two binding equilibria. If the enantiomers of carvone bind equally well to an “achiral” receptor, no differentiation occurs.

So to return to the Shusterman Paradox, is the statement “raise your right hand” chiral? When it enters your brain, it leads to a different set of events than “raise your left hand”.

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