Title: Gramicidin S
CAS Registry Number: 113-73-5
Additional Names: Gramicidin S (Soviet); gramicidin C (Soviet)
Molecular Formula: C60H92N12O10
Molecular Weight: 1141.45
Percent Composition: C 63.13%, H 8.12%, N 14.73%, O 14.02%
Literature References: Cyclic decapeptide antibiotic produced by a strain of Bacillus brevis. Isoln: Gause et al., Compt. Rend. Acad. Sci. USSR 43, 217 (1944), C.A. 39, 1195 (1945); Gause, Brazhnikova, Lancet 247, 715 (1944). More closely related to tyrocidines in biological and chemical properties than to true gramicidins, q.q.v. Structure: Synge, Biochem. J. 39, 363 (1945); Consden et al., ibid. 40, xliii (1946); 41, 596 (1947); Battersby, Craig, J. Am. Chem. Soc. 73, 1887 (1951); Erlanger, Goode, Nature 174, 840 (1954). Synthesis and absorption spectrum: Schwyzer, Sieber, Helv. Chim. Acta 40, 624 (1957); Waki, Izuniya, Bull. Chem. Soc. Jpn. 40, 1687 (1967). Solid phase synthesis: Losse, Neubert, Tetrahedron Lett. 1970, 1267; M. Ohno et al., J. Am. Chem. Soc. 93, 5251 (1971). Improved synthesis via a linear pentapeptide: Y. Minematsu et al., Tetrahedron Lett. 1980, 2179; via a linear decapeptide: T. Mukaiyama et al., Chem. Lett. 1981, 1367. Industrial procedure: GB 836725 (1960 to Ciba). Review: Y. A. Ovchinnikov, V. T. Ivanov, "The Cyclic Peptides: Structure, Conformation, and Function" in The Proteins vol. V, H. Neurath, R. L. Hill, Eds. (Academic Press, New York, 3rd ed., 1982) pp 547-555.
Derivative Type: Hydrochloride
Molecular Formula: C60H92N12O10.2HCl
Molecular Weight: 1214.37
Percent Composition: C 59.34%, H 7.80%, N 13.84%, O 13.18%, Cl 5.84%
Properties: Prisms from ethanol + aq HCl, dec 277-278°. [a]D24 -289° (c = 0.43 in 70% ethanol). Freely sol in alcohol; slightly sol in acetone. Practically insol in water, acids, alkalies. LD50 i.p. in rats: 17 mg/kg (Gause, Brazhnikova).
Optical Rotation: [a]D24 -289° (c = 0.43 in 70% ethanol)
Toxicity data: LD50 i.p. in rats: 17 mg/kg (Gause, Brazhnikova)
Therap-Cat: Topical antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides. |