Biochemistry of Amino Acids - A. Meister 1961

The Role of Amino Acids in Nutrition
Amino Acid Antagonists
Glutamic Acid Antagonists

Several years ago, it was observed that Methionine sulfoxide inhibits the growth of Lactobacillus arabinosus in the presence of glutamic acid in the nutrient medium, but exerts no such effect when glutamic acid is replaced by glutamine [191]:

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Further studies demonstrated that this antagonist competitively inhibits the enzymatic Synthesis of Glutamine from glutamic acid [193]. Interestingly, L-methionine sulfoxide is more active than D-methionine sulfoxide, and activity differences also exist between the sulfoxide stereoisomers of L-methionine sulfoxide [192]. When tested for their effect on bacterial growth, ethionine sulfoxide and A number of its higher homologs proved to be less active antagonists of glutamic acid than methionine sulfoxide. β-Hydroxyglutamic acid also inhibits growth [195]; apparently, only one of its stereoisomers exhibits activity [196]. α-Methylglutamic acid inhibits the action of Escherichia coli L-glutamate decarboxylase when the analogue is incubated with the enzyme prior to The addition of glutamic acid. When the inhibitor and substrate are added simultaneously, only slight inhibition is observed, which is apparently caused by The formation of an enzyme-inhibitor complex [199]. α-Methylglutamic acid also inhibits dog Kidney glutaminase, though the L- and D-isomers of glutamic acid inhibit this enzyme to nearly the same degree [200].