Amino Acid Analogs III: New Syntheses of Monomethyl- and Monophenylglutamic Acids

Glutamic acid analogs containing 3- and 4-methyl and 2-, 3-, and 4-phenyl substituents were prepared. The 3- and 4-methyl- and 3- and 4-phenylglutamic acids did not inhibit Plasmodium berghei and were nontoxic to the host (mice) at 640 mg/kg. The five analogs in addition to 2-methylglutamic acid were inactive against Lactobacillus casei at 1000 μg/ml in a defined medium; against Escherichia coli, only 2-methylglutamic acid caused 27% inhibition at 10, 000 μg/ml. All six analogs failed to inhibit Aspergillus niger, Aspergillus oryzae, Trichoderma viride, and Myrothecium verrucaria in a defined medium below 10,000 μg/ml.