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Unequal Activities of Enantiomers via Biological Receptors: Examples of Chiral Drug, Pesticide, and Fragrance Molecules

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Albrecht Mannschreck and Roland Kiesswetter

Department of Organic Chemistry, University of Regensburg, D-93040 Regensburg, Germany

Erwin von Angerer

Department of Pharmacy, University of Regensburg, D-93040 Regensburg, Germany

J. Chem. Educ., 2007, 84 (12), p 2012

DOI: 10.1021/ed084p2012

Publication Date (Web): December 1, 2007

Section:

History, Education, and Documentation

Abstract

A molecule coming from outside an organism can form a ligand–receptor complex. Upon its formation, a message is transmitted, for example, to certain cells. In this way, two enantiomers can emit messages that differ, either quantitatively or qualitatively. In the present article, these facts are taken as a common basis for the actions of chiral drug, pesticide, and fragrance molecules. For each of these groups, a few examples of current interest were selected. At present, the demand for single enantiomers in medicine and agriculture is economically highly significant. We propose a two-hour lecture, emphasizing the similarity between the different types of receptor-mediated actions of enantiomers, thus connecting some seemingly unrelated subjects in the university curricula. The lecture is intended for medicinal chemistry students; in addition, it should be suitable for the third-year chemistry students who are interested in the applications presented here.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Biochemistry

Keywords (Pedagogy):

Analogies / Transfer

Keywords (Subject):

Agricultural Chemistry

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

The Enantioselectivity of Odor Sensation: Some Examples for Undergraduate Chemistry Courses
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- The Enantioselectivity of Odor Sensation: Some Examples for Undergraduate Chemistry Courses
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  Journal of Chemical Education2010 87 (6), 598-603
  This article discusses seven chiral odorants that demonstrate the enantioselectivity of odor sensation: carvone, Celery Ketone, camphor, Florhydral, 3-methyl-3-sulfanylhexan-1-ol, muscone, and methyl jasmonate. After a general introduction of the odorant−...
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The Metolachlor Herbicide: An Exercise in Today's Stereochemistry
Albrecht Mannschreck , Erwin von Angerer
Journal of Chemical Education2009 86 (9), 1054
- The Metolachlor Herbicide: An Exercise in Today's Stereochemistry
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  Journal of Chemical Education2009 86 (9), 1054
  Metolachlor is one of the most widely used agents registered for the protection of many cultivated plants against weeds. Because of axial and central chirality, this molecule forms four stereoisomers, the investigation of which by 1H NMR and ...
  Abstract | Hi-Res PDF | PDF w/ Links
Unequal Activities of Enantiomers via Biological Receptors: Examples of Chiral Drug, Pesticide, and Fragrance Molecules
Albrecht Mannschreck and Roland Kiesswetter , Erwin von Angerer
Journal of Chemical Education2007 84 (12), 2012
- Unequal Activities of Enantiomers via Biological Receptors: Examples of Chiral Drug, Pesticide, and Fragrance Molecules
  Albrecht Mannschreck and Roland Kiesswetter , Erwin von Angerer
  Journal of Chemical Education2007 84 (12), 2012
  A molecule coming from outside an organism can form a ligand–receptor complex. Upon its formation, a message is transmitted, for example, to certain cells. In this way, two enantiomers can emit messages that differ, either quantitatively or qualitatively. ...
  Abstract | Hi-Res PDF | PDF w/ Links
Collection of Chrial Drug, Pesticide, and Fragrance Molecular Models
William F. Coleman
Journal of Chemical Education2007 84 (12), 2018
- Collection of Chrial Drug, Pesticide, and Fragrance Molecular Models
  William F. Coleman
  Journal of Chemical Education2007 84 (12), 2018
  This month’s Featured Molecules include (S)-citalopram, (S,S)-ethambutol, (R)-cetirizine, (S)-sulpiride, (R)-mecoprop, (S,M)-metolachlor, (R)-metalaxyl, (S,P)-metolachior, indoxacarb, (R)-lilial, (4S,7R)-galaxolide, (R)-1-p-menthene-8-ol, R-1-p-menthene-8-...
  Abstract | Hi-Res PDF | PDF w/ Links