TETRONOMYCIN, A NOVEL POLYETHER OF UNUSUAL STRUCTURE

Tetronomycin, C34H50O8, isolated from a strain of Streptomyces sp. nov. represents a novel polycyclic ionophore polyether. The crystal structure and absolute configuration were established by X-ray analysis of the mono-O-acetyltetronomycin silver salt. Tetronomycin is the first metabolic polyether w...

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Published inJournal of antibiotics Vol. 35; no. 2; pp. 142 - 150
Main Authors KELLER-JUSLÉN, CAMILLA, KING, HAMILTON D., KUHN, MAX, LOOSLI, HANS-RUDOLF, PACHE, WALTER, PETCHER, TREVOR J., WEBER, HANS PETER, WARTBURG, ALBERT VON
Format Journal Article
LanguageEnglish
Published Japan JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 01.01.1982
Subjects
Anti-Bacterial Agents - isolation & purification
Anti-Bacterial Agents - pharmacology
Chemical Phenomena
Chemistry
Ethers - isolation & purification
Ethers - pharmacology
Fermentation
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Streptomyces
Streptomyces - metabolism
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Summary:Tetronomycin, C34H50O8, isolated from a strain of Streptomyces sp. nov. represents a novel polycyclic ionophore polyether. The crystal structure and absolute configuration were established by X-ray analysis of the mono-O-acetyltetronomycin silver salt. Tetronomycin is the first metabolic polyether which contains a tetronic acid moiety instead of the essential carboxylic acid function. A trisubstituted cyclohexane ring and an interesting molecular conformation of the silver salt represent additional unique structural features. Extensive NMR-studies enabled the assignment of chemical shifts and the correlation of the proton and carbon signals. Tetronomycin exhibits activity against Gram-positive bacteria.
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.35.142