In the Classroom edited by
Featured Molecules
William F. Coleman Wellesley College Wellesley, MA 02481
Enantiomer Specificity in Pharmaceuticals William F. Coleman Department of Chemistry, Wellesley College, Wellesley, MA 02481;
[email protected] July Featured Molecules The molecules of the month this month come from three papers: “Demonstration of Enantiomer Specificity of Proteins and Drugs” by Gretchen L. Anderson (pages 971–974), “Incorporation of Medicinal Chemistry into the Organic Chemistry Curriculum” by David C. Forbes (pages 975–976), 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 (pages 977–980). 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 and other molecules are available at the Only@JCE Online Web site: http://www.JCE.DivCHED.org/JCEWWW/Features/ MonthlyMolecules/2004/Jul/
(R)-ibuprofen (R)-naproxen
(S)-naproxen
(S)-ibuprofen
(R)-thalidomide
(S)-thalidomide Paxil (paroxetine HCl)
www.JCE.DivCHED.org
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Vol. 81 No. 7 July 2004
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Journal of Chemical Education
981
