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.
In addition to the static image, two fully manipulable versions (Jmol, MDLChime)
of these molecules appear below. (The Jmol versions may take a few extra seconds
to load, based on the speed of your Internet connection.)
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