Biochemistry of Amino Acids - A. Meister 1961

Naturally Occurring Amino Acids
Peptides and Related Compounds
Antibiotics

Peptide bonds and Amino Acids have been discovered in the molecules of numerous Antibiotics, which has spurred the intensive development of peptide chemistry in recent years [420].

As mentioned above, certain antibiotics contain D-amino acid residues; in addition, several novel amino acids have been identified within their composition. Penicillins contain D-penicillamine, which can be viewed as a derivative of D-valine or D-Cysteine [374, 421].

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Chloramphenicol (levomycetin), a structural analogue of phenylalanine, is stereochemically a derivative of D-threo-β-phenylserine [422]:

Bacillus subtilis produces two Peptides with antibiotic activity: subtilin and bacitracin. Subtilin is composed of Glycine, Alanine, valine, leucine, isoleucine, Proline, phenylalanine, Tyrosine, Lysine, aspartic and glutamic acids, mesolanthionine, and “methyl-lanthionine” (p. 53) [423]. Bacitracin preparations consist of several components; upon acid Hydrolysis, one of them breaks down to yield cystine, Ornithine, lysine, phenylalanine, aspartic acid, isoleucine, leucine, and glutamic acid [424].

The tyrocidine and gramicidin groups of antibiotics are cyclic peptides containing D-amino acid residues. For purified tyrocidin A, the following empirical formula has been established: (D-phenylalanine) 2, L-phenylalanine, L-valine, L-tyrosine, L-leucine, L-proline, L-ornithine, L-glutamine, L-asparagine [365, 375, 376, 378, 425]. Much attention has been focused on the polymyxin group, which also includes aerosporin and circulin. These antibiotics contain L-α,γ-diaminobutyric acid; D-Serine and D-leucine have also been detected in their hydrolysis products [426]. The hydrolysis products of antibiotics belonging to the actinomycin group were found to contain N-methylvaline, Sarcosine, allo-D-isoleucine (p. 68), and D-valine [382, 383]. Among the hydrolysis products of the antibiotic cephalosporin N, D-δ-amino-δ-carboxyvalerylglycine [369, 370]—a derivative of the δ-amide of D-α-aminoadipic acid [45, 357]—was discovered. The isolated compound

δ-Amino-δ-carboxyvalerylglycine

can be regarded as a higher homologue of γ-D-glutamylglycine. Using chromatographic analysis, γ-glutamylalanine was detected in pea seedlings [427].



Last update: 06/08/2026

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