Antibiotics A21459 A and B, New Inhibitors of Bacterial Protein Synthesis: II. Structure Elucidation

The structures of the antibiotics, active against a few Gram-negative bacteria and Clostridium difficile, were determined on the basis of physicochemical analyses on the intact molecules and on the acid hydrolysate of A21459 A. FAB-MS and 1H and 13C NMR investigations identified the amino acid units...

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Bibliographic Details
Published in:Journal of antibiotics 1996/02/25, Vol.49(2), pp.150-154
Main Authors: FERRARI, P., VÉKEY, K., GALIMBERTI, M., GALLO, G. G., SELVA, E., ZERILLI, L. F.
Format: Article
Language:English
Subjects:
Amino Acid Sequence
Amino Acids - analysis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Antibiotics (antibacterial agents, antifungal agents)
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Applied microbiology
Biological and medical sciences
Fundamental and applied biological sciences. Psychology
Microbiology
Peptides, Cyclic - chemistry
Peptides, Cyclic - pharmacology
Spectrum Analysis
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Summary:The structures of the antibiotics, active against a few Gram-negative bacteria and Clostridium difficile, were determined on the basis of physicochemical analyses on the intact molecules and on the acid hydrolysate of A21459 A. FAB-MS and 1H and 13C NMR investigations identified the amino acid units and determined their sequence. Antibiotics A21459 A and B are homodetic cyclic peptides constituted by eight amino acid units. They are glycine, methoxytryptophan, tryptophan, cysteine, alanine, sarcosine, dehydroalanine, and α-aminobutyric acid for A21459 A (alanine for A21459 B). Cysteine and alanine condensed to form a thiazole moiety, according to the biosynthesis of thiazole containing antibiotics.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.49.150