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  Home > JCE Print > Journal of Chemical Education > Issues > 2004  > March  >
Information, Textbooks, Media, Resources
Featured Molecules
Bioorganic Synthesis: Monosodium Glutamate and Other Amino Acids
William F. Coleman
Chemistry Department, Wellesley College, Wellesley, MA 02481
Cover
March 2004
Vol. 81 No. 3
p. 448
Full Text
The March featured molecules are discussed in the article “The Monosodium Glutamate Story: The Commercial Production of MSG and Other Amino Acids”. This paper provides a number of opportunities for introducing students to the importance of stereochemistry in bioorganic synthesis. The collection here includes all of the relevant molecules in the synthesis of α-amino-ε-aminocaprolactam (ACL). The introduction of two chiral centers in the reaction of cyclohexene with NOCl results in four diastereomers, and it is instructive to ask students to predict the relative abundance of those isomers and the dependence of that distribution on the extent to which the reaction is syn- or anti-addition, and to account for the fact that the resultant oxime, and the ACL, are obtained as racemates.

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

Image of molecule.

Figure 1. (S)-glutamic acid molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 2. (R)-glutamic acid molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 3. α,ε-diaminopimelic acid molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

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

Figure 5. 5–(β–methylthioethyl)hydantoin molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

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

Image of molecule.

Figure 7. (R)-methionine molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 8. Cyclohexanol molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 9. Cyclohexene molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 10. Oxime of 2-amino-cyclohexanone molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 11. (S)-α-amino-ε-aminocaprolactam molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

Figure 12. (R)-α-amino-ε-aminocaprolactam molecule. Interactive Chime-based structure (top); static structure graphic (bottom)

Image of molecule.

(R,R)

Image of molecule.

(R,S)

Image of molecule.

(S,R)

 

Image of molecule.

(S,S)

 

Figures 13-16. Nitrosochlorides of cyclohexene molecules. Interactive Chime-based structures (top); static structure graphics (bottom)
More Information
*  Citation
 Coleman, William F. J. Chem. Educ. 2004 81 448.
*  Keywords
 Internet / Web-Based Materials; Molecular Modeling / Dynamics; Molecular Properties / Structure; Multimedia; Teaching / Learning Aids
*  History
 Created:
Last Updated:		 February 3, 2004
February 18, 2005
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