A21978C, a complex of new acidic peptide antibiotics. Isolation, chemistry, and mass spectral structure elucidation
| Autor: | Manuel Debono, D. S. Fukuda, Jules A. Hoffmann, C. B. Carrell, Bernard J. Abbott, K. Biemann, R. L. Hamill, W. C. Herlihy, John L. Occolowitz, Mitchell Barnhart |
|---|---|
| Rok vydání: | 1987 |
| Předmět: |
Magnetic Resonance Spectroscopy
Streptomyces roseosporus Chemical Phenomena Stereochemistry Acylation Molecular Conformation Peptide Peptides Cyclic Gas Chromatography-Mass Spectrometry Mass Spectrometry Hydrolysis Drug Discovery Amino Acid Sequence Amino Acids Peptide sequence Chromatography High Pressure Liquid Pharmacology chemistry.chemical_classification Chromatography biology Edman degradation Chemistry Fatty Acids Fatty acid biology.organism_classification Streptomyces Anti-Bacterial Agents Amino acid Spectrophotometry Intercellular Signaling Peptides and Proteins Peptides |
| Zdroj: | The Journal of Antibiotics. 40:761-777 |
| ISSN: | 1881-1469 0021-8820 |
| DOI: | 10.7164/antibiotics.40.761 |
| Popis: | A21978C, produced by Streptomyces roseosporus, NRRL 11379, is a complex of new acidic lipopeptolide antibiotics which inhibits Gram-positive bacteria. HPLC separation of the various components from the purified complex resulted in the isolation of A21978C1, -C2 and -C3 (major components) and -C4, -C5, and -C0 (minor components). Each of these components was fermented with cultures of Actinoplanes utahensis (NRRL 12052) to give the identical inactive peptide ("A21978C nucleus") by removal of the fatty acid acyl groups from the N-terminus. This peptide was composed of 13 amino acids: L-kynurenine, L-threo-3-methylglutamic acid, L-asparagine, L-aspartic acid (3 residues), glycine (2 residues), L-tryptophan, L-ornithine, D-alanine, D-serine and L-threonine. The amino acid sequence was determined using a combination of the Edman degradation and gas chromatography mass spectrum (GC-MS) analysis of appropriately derivatized peptides obtained from partial hydrolysis. Each major component was shown to be acylated with a branched chain fatty acid at the N-terminus and the structure of this fatty acid was determined by 1H NMR and mass spectral methods. A structure for A21978C was assigned on the basis of this degradative and physico-chemical information. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|