Bioorganic Synthesis: Monosodium Glutamate and Other Amino Acids

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Featured Molecules

William F. Coleman Wellesley College Wellesley, MA 02481

Bioorganic Synthesis: Monosodium Glutamate and Other Amino Acids March Featured Molecules The March featured molecules are discussed in the article “The Monosodium Glutamate Story: The Commercial Production of MSG and Other Amino Acids” on pages 347– 355. 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), shown on page 350. 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 and other molecules are available at the Only@JCE Online Web site: http://www.JCE.DivCHED.org/JCEWWW/Features/ MonthlyMolecules/2004/Mar/

β-methylthiopropionaldehyde

(S)-glutamic acid

(R)-glutamic acid

(S)-methionine

(R)-methionine

5-(β-methylthioethyl)hydantoin

α,ε-diaminopimelic acid

(S)-α-aminoε-aminocaprolactam

cyclohexanol

oxime of 2-aminocyclohexanone

cyclohexene

(R)-α-aminoε-aminocaprolactam

nitrosochlorides of cyclohexene

448

Journal of Chemical Education

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Vol. 81 No. 3 March 2004

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www.JCE.DivCHED.org