Odour character differences for enantiomers correlate with molecular flexibility.
The olfactory system sensitively discerns scents from many small molecules as the brain analyses signals from nasal receptors. These receptors are selective to some degree, though the mechanism for selectivity is still controversial. Enantiomers, chiral pairs of left- and right-handed structures, are an important class of molecules in assessing proposed mechanisms. We show that there is a correlation between molecular (structural) flexibility and whether or not the left- and right-handed enantiomers smell the same. In particular, for the fairly extensive class of enantiomers with six-membered ring flexibility, enantiomers do not smell the same. There are, of course, significant experimental uncertainties, which we discuss here. We discuss models of receptor selectivity, both those based on shape and those where discrimination is based on other factors, such as electron affinity, proton affinity or vibration frequencies. The differences in scent of these enantiomers appear to be consistent with simple generalizations of a 'swipe card' model in which, while the shape must be good enough, critical information for actuation is a separate factor.
Brookes
Jennifer C
JC
Department of Physics and Astronomy, University College London, Gower Street, London WC1E 6BT, UK. ucapjcb@ucl.ac.uk
Horsfield
A P
AP
Stoneham
A M
AM
D003198:Computer Simulation; D015394:Molecular Structure; D009812:Odorants; D018035:Receptors, Odorant / Q000737:chemistry*; D012903:Smell / Q000502:physiology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D018035:Receptors, Odorant