Thiostrepton
Title: Thiostrepton
CAS Registry Number: 1393-48-2
Trademarks: Bryamycin (BMS); Thiactin
Molecular Formula: C72H85N19O18S5
Molecular Weight: 1664.89
Percent Composition: C 51.94%, H 5.15%, N 15.98%, O 17.30%, S 9.63%
Literature 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°. [a]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).
Optical Rotation: [a]D23 -98.5° (glacial acetic acid); -61° (dioxane); -20° (pyridine)
Absorption maximum: uv maxima but shows characteristic shoulders at 225, 250, 280 nm (E1%1cm 520, 380, 255)
 
Derivative Type: Hemisuccinate
Literature References: Prepn: Bodanszky, Fried, US 3181995 (1965 to Olin Mathieson).
Properties: mp 200-220°, forms a water-soluble potassium salt.
Melting point: mp 200-220°
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.

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