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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > July  >
In the Classroom
Featured Molecules
Enantiomer Specificity in Pharmaceuticals
William F. Coleman
Department of Chemistry, Wellesley College, Wellesley, MA 02481

Cover
July 2004
Vol. 81 No. 7
p. 981

Full Text
The molecules of the month this month come from three papers: “Demonstration of Enantiomer Specificity of Proteins and Drugs” by Gretchen L. Anderson, “Incorporation of Medicinal Chemistry into the Organic Chemistry Curriculum” by David C. Forbes, and “Infusing the Chemistry Curriculum with Green Chemistry Using Real-World Examples, Web Modules, and Atom Economy in Organic Chemistry Courses” by Michael C. Cann and Trudy A. Dickneider.

The authors of these papers use molecules whose names at least are familiar to the majority of students to introduce important structural and synthetic concepts. A particularly poignant example is that of thalidomide, in which the two enantiomers produce dramatically, and in the case of the S form tragically, different results. In addition to demonstrating enantiospecific reactivity, the thalidomide case is a good starting point for a discussion of how chemists ask questions, what questions we should be asking, and whether or not it is possible to minimize, if not completely eliminate, unintended consequences.

Fully manipulable (Chime) versions of these molecules appear below. These and other molecules are available Only@JCE Online.

Image of molecule.

Figure 1. (R)-ibuprofen molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 2. (S)-ibuprofen molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 3. (R)-naproxen molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 4. (S)-naproxen molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Figure 5. (R)-thalidomide molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Figure 6. (S)-thalidomide molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 7. Paxil (paroxetine HCl) molecule. Interactive Chime-based structures (top); static structure graphics (bottom)

 

More Information
*  Citation
Coleman, William F. J. Chem. Educ. 2004 81 981.
*  Keywords
Internet / Web-Based Materials; Molecular Modeling / Dynamics; Molecular Properties / Structure
*  History
Created:
Last Updated:
May 27, 2004
January 19, 2005
  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > July  > Page 981


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