Orgo Unit 5.1 Discussion

Orgo Unit 5.1 Discussion - “chiral environment” for the...

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Topic # 1 Carvone exists as a pair of enantiomers (see structure p 23). (R)-(-)-carvone smells like spearment, whereas (S)-(+)-carvone smells like caraway. Why do these enantiomers have different smells (i.e., different biological activity). In our textbook, Organic Chemistry with Biological Applications-2 nd Edition , McMurry discusses in Chapter 5 the factors that can lead to different biological properties of organic molecules. As an example, he cites (+)- Limonene, which has a citrus scent, versus (-)-Limonene, which has a pine scent. Accounting for this, he discusses the importance of biological receptors, which have a specific shape that may only allow one enantiomer of a chiral substrate to fit in. This specificity arises from how the receptor provides a
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Unformatted text preview: “chiral environment” for the substrate, which distinguishes between enantiomers of chiral compounds. In the absence of chiral environments, enantiomers are chemically identical. In the case of carvone, the chiral environment for the enantiomers are likely to be provided by our olfactory receptors. Because we are able to detect the two different odors, the implication is that we have chrial receptors as well for detecting each enantiomer. References: Leitereg, T. J., Guadagni, D. G., Harris, J., Mon, T. R., & Teranishi, R. (1971). Chemical and Sensory Data Supporting the Difference between the Odors of the Enantiomeric Carvones. J. Agr. Food Chem., 19, 4, 785-787....
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