Streptothricins
Title: Streptothricins
Additional Names: Racemomycins; yazumycins
Literature References: A mixture of antibiotics, originally thought to be a single substance, differing only in the number of repeating residues in the peptide side chain. Streptothricins F, E, D, C, B, A, and X are known and have 1 to 7 b-lysine residues resp.: Khokhlov, Shutova, J. Antibiot. 25, 501 (1972). Separation of isomers: Khokhlov, Reshetov, J. Chromatogr. 14, 495 (1964). Identity with racemomycins: H. Taniyama et al., Chem. Pharm. Bull. 19, 1627 (1971). Identity with yazumycins: eidem, J. Antibiot. 24, 390 (1971). Activity studies: Germanova, Goncharskaya, Antibiotiki 14, 48, 137 (1969), C.A. 70, 66547, 85906t (1969). Biosynthetic studies: Voronina et al., ibid. 1063, C.A. 72, 77387a (1970); Y. Sawada et al., Chem. Pharm. Bull. 26, 885 (1978). Partial syntheses: M. Kinoshita, Y. Suzuki, Bull. Chem. Soc. Jpn. 50, 2375 (1977); S. Kusumoto et al., Chem. Lett. 1981, 1317. Prepn of semi-synthetic racemomycins: Y. Sawada, H. Taniyama, Chem. Pharm. Bull. 25, 1302 (1977). Streptolin was formerly used for the streptothricin components where n equals 2 or 3.
 
Derivative Type: Streptothricin F
Additional Names: Racemomycin A; streptothricin VI; yazumycin A
Molecular Formula: C19H34N8O8
Molecular Weight: 502.52
Percent Composition: C 45.41%, H 6.82%, N 22.30%, O 25.47%
Literature References: n = 1. Originally known as streptothricin. Produced by variants of Actinomyces lavendulae. Isoln: Waksman, Woodruff, Proc. Soc. Exp. Biol. Med. 49, 207 (1942). Purification: Peck et al., J. Am. Chem. Soc. 68, 772 (1946); Kocholaty, Junowicz-Kocholaty, Arch. Biochem. 15, 55 (1947). Identity with streptothricin VI: Hutchinson et al., Arch. Biochem. 22, 16 (1949); Swart, J. Am. Chem. Soc. 71, 2942 (1949). Prepn: Carter et al., J. Am. Chem. Soc. 76, 566 (1954). Structure: van Tamelen et al., ibid. 83, 4295 (1961); Johnson, Westley, J. Chem. Soc. 1962, 1642. Revised structure: S. Kusumoto et al., J. Antibiot. 35, 925 (1982). Biosynthesis: S. J. Gould et al., J. Am. Chem. Soc. 103, 2871 (1981). Total synthesis: S. Kusumoto et al., Tetrahedron Lett. 23, 2961 (1982).
Properties: Amorphous, white powder. Thermostable. Water sol; slightly sol in most organic solvents. Stable between pH 1 and 8.5. LD50 i.v. in mice: 300 mg/kg (Taniyama).
Toxicity data: LD50 i.v. in mice: 300 mg/kg (Taniyama)
 
Derivative Type: Hydrochloride
Properties: White powder. [a]D25 -51.3° (c = 1.4). Sol in water and dil mineral acids. Practically insol in ether, petr ether, chloroform.
Optical Rotation: [a]D25 -51.3° (c = 1.4)

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