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JCE Featured Molecules
William F. Coleman
Molecular Models of Natural Products November Featured Molecules This month’s issue of the Journal includes several papers discussing interesting molecules that fall into the broad category of natural products, and four of these papers serve as the source for our featured molecules this time around. Addison Ault weaves an interesting tale of the search for the true structure of eserethole and of the competition between two research groups—that of Percy Julian, consisting of two people, and that of the British chemist Robert Robinson, a large group at Oxford (1). David Vosburg describes a case study approach to teaching organic synthesis and includes a number of molecules that have been the basis of student research papers (2). Jean-Michel Lavoie, Esteban Chornet, and André Pelletier have developed an experiment utilizing GC–MS to separate terpenes from citrus (3), and Patty Feist, in a paper that may send readers running for their Kafka, has students synthesize a cockroach pheromone that may have wide applicability in cockroach control without the problems created by many insecticides (4). The molecules that have been added to our collection contain a wide variety of functional groups, and would serve as a good source for an exercise in having students recognize these functional groups in a number of different settings. Questions such as “How many cyclic ether groups are present?”, “How many bridgehead carbons?”, or “How many chiral centers?” would be useful exercises in organic and introductory nonmajors courses. Students could find other pheromone structures and see how they compare with that of blattellaquinone, or explore the various ways in which the steroid backbone shows up in the collection. This collection of molecules also provides a good starting point for students to use the capabilities of Jmol to further explore structural features. The focus here is on measuring bond distance and angles. Double clicking on any atom will change
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the cursor to a cross-hair (this may take a little practice). One end of a dashed line is now locked to that atom. Dragging the free end of the line to other atoms will show the distance between the two centers in nanometers. Double clicking on a second atom will lock a line segment between those two atoms and display the distance in black. There is now another free end of the segmented line, and dragging that to any other atom will show the angle defined by the three-atom combination. Double clicking on the third atom fixes the second line segment and gives a third segment that can be dragged and double clicked to display dihedral angles. Students could, for example, explore various ring structures in this collection to determine which rings are distorted and which are not. The files that are currently used for the collection are MDL mol files, and do not contain orbital, electrostatic potential, or vibrational data. Beginning next month we will change the file format, and that information will be available to users, either through the Jmol menu (right click on any structure) or through menu choices. Not all of the molecules from the Ault paper (1) have been included, leaving room for students to model and perform calculations on many of the non-eserethole species, and to consider how modern tools of analysis might have simplified the identification of eserethole. They might also wish to determine which pair of eserethole enantiomers are the more stable. (The eserethole structures included here have all been optimized at the 6311++G (d,p) level.) Literature Cited 1. Ault, A. J. Chem. Educ. 2008, 85, 1524–1530. 2. Vosburg. D. J. Chem. Educ. 2008, 85, 1519–1523. 3. Lavoie, J.-M.; Chornet, E.; Pelletier, A. J. Chem. Educ. 2008, 85, 1555–1557. 4. Feist, P. J. Chem. Educ. 2008, 85, 1548–1549.
Supporting JCE Online Material
http://www.jce.divched.org/Journal/Issues/2008/Nov/abs1584.html Full text (HTML and PDF) with images in color Links to cited URLs and JCE articles Supplement Blattellaquinone, a sex pheromone of the German cockroach (Blattella germanica), is secreted by females to attract male cockroaches (4).
Find “Molecular Models of Natural Products” in the JCE Digital Library at http://www.JCE.DivCHED.org/JCEWWW/Features/ MonthlyMolecules/2008/Nov/
The molecules added to the collection this month are from ref 1: 2 pairs of eserethole enantiomers from ref 2: camptothecin; dehydrocholic acid; dextromethorphan; estrone; grandisine D; O-methylpsychotrine; ouabagenin; penicillin V; progesterone; prostaglandin; pyrethrin I; quinine; salvinorin A; Tamiflu; tetracycline
(R)-Limonene is a secondary metabolite found in citrus fruit peels (3).
1584
from ref 3:(R)-limonene; (R)-linalool; β-myrcene; α-pinene from ref 4 (Scheme 1): 2,5-dimethoxybenzyl alcohol; 2,5-dimethoxybenzyl 3-methylbutanoate; blattellaquinone
Journal of Chemical Education • Vol. 85 No. 11 November 2008 • www.JCE.DivCHED.org • © Division of Chemical Education
