9364. Thiostrepton
Nomenclature
Description and references
Polypeptide antibiotic contg sulfur. Produced by Streptomyces azureus isolated from New Mexican soil: Pagano et al., Antibiot. Annu. 1955-56, 554; Vandeputte, Dutcher, ibid. 560; GB 795570 (1958); Donovick et al.; Platt, US 2982689; US 2982698 (1961 all to Olin Mathieson). Structure studies: Bodanszky et al., J. Am. Chem. Soc. 84, 2003 (1962); 86, 2478 (1964); Anderson et al., Nature 225, 233 (1970). Total structure determn: K. Tori et al., Tetrahedron Lett. 1976, 185; eidem, J. Antibiot. 32, 1072 (1979). 13C-NMR study: eidem, ibid. 34, 124 (1981). Total synthesis: K. C. Nicolaou et al., Angew. Chem. Int. Ed. 43, 5087, 5092 (2004). Mode of action as an inhibitor of protein synthesis: Cannon, Burns, FEBS Lett. 18, 1 (1971); Cundliffe, Biochem. Biophys. Res. Commun. 44, 912 (1971). Identity with thiactin: Bodanszky et al., J. Antibiot. 16A, 76 (1963). Comprehensive description: K. Florey, Anal. Profiles Drug Subs. 7, 423-444 (1978). Review: Pestka, Bodley, in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 551-573; E. Cundliffe, ibid. vol. 5 (pt. 1), F. E. Hahn, Ed. (1979) pp 329-343.
Properties
Crystals from chloroform + methanol, dec 246-256°. [α]D23 98.5° (glacial acetic acid); 61° (dioxane); 20° (pyridine). Sol in chloroform, dioxane, pyridine, glacial acetic acid, DMF. Practically insol in water, the lower alcohols, nonpolar organic solvents, dil aq acid or base. Dissolved by methanolic acid or base with decompn. Stable in the presence of gastric and intestinal juices and urine. No uv maxima but shows characteristic shoulders at 225, 250, 280 nm (E1%1cm 520, 380, 255).Derivative
Hemisuccinate.Description and references
Prepn: Bodanszky, Fried, US 3181995 (1965 to Olin Mathieson).
Properties
mp 200-220°, forms a water-soluble potassium salt.Therapeutic Category
Antibacterial.
Therapeutic Category (Veterinary)
Antibacterial.Keywords
Antibacterial (Antibiotics); Polypeptides