Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 128, Issue 4, Pages 1346-1352Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja057483x
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Georgyone (1) and arborone (2), powerful woody odorants, have been synthesized enantioselectively along with their enantiomers. Several structural relatives of 1 and 2 have also been made enantioselectivity in order to probe the molecular details of the binding of 1 and 2 to the olfactory G-protein-coupled receptors which they activate. These studies have led to a number of conclusions regarding the structural requirements for woody odor, including absolute configuration, critical methyl substitution, and the spatial orientation of the key methyl groups. Odorants 1 and 2 bind to at least 10 mouse olfactory receptors, lending support to the combinatorial model for odor perception/differentiation. The implications of this work with regard to possible receptor binding modes are discussed.
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