Preparation and antibacterial action of some compounds structurally related to glutamic acid. Their application in microbiological determination of small quantities of glutamine

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Abstract
A number of substances structurally related to glutamic acid has been prepd., including the hydrazide, R.CO.NH.NH2; its acetone derivative, R.CO.N. H.N:C(CH3)2; its benzaldehyde derivative, R.CO.NH.N:CH. C6H5; the hydroxamic acid, R.CO.NHOH; and an analogous sulphoxide, R.SO.CH3 and sulphone, R.SO2.CH3. (R = -CH2.CH2.CH(NH2). COOH). The hydrazide and hydroxamic acid similarly related to aspartic acid have also been prepd. Some of these compounds, and also other substances related to glutamic acid (especially homologues of glutamic acid), had no effect on growth and glycolysis of streptococci. Those formulated above, except the benzaldehyde derivative and the sulphone (which, however, inhibited Escherichia coli), inhibited streptococcal growth. The basis for the action of the hydroxamic acid is unknown, but action of the other compounds on streptococci is related to the metabolism of glutamine or of glutamic acid. Inhibition by the sulphoxide has been applied in the microbiological detn. of glutamine. Glutamic acid can to some extent replace glutamine in growth of streptococci in ordinary media, but the sulphoxide (0.01 [image]) prevents this and results in a prompt and adequately stable growth of the organisms in the presence of 5-40 micromol. of glutamine in 7 ml. of medium. Photometric measurement of the resulting growth has been used to determine glutamine in natural materials.