Structural Formula Vector Image
Title: Gramicidin(s)
Additional Names: Gramicidin D (Dubos); linear gramicidins
Trademarks: Gramoderm (Schering)
Literature References: Polypeptide antibiotic complex first isolated from the mixture tyrothricin along with tyrocidine, q.q.v. from cultures of Bacillus brevis: Dubos, Hotchkiss, J. Exp. Med. 73, 629 (1941); eidem, J. Biol. Chem. 141, 155 (1941). Commercial extraction: Baron, US 2534541 (1950 to Penick). Commercial preparation is a mixture of the four components, gramicidin A, B, C, and D, comprising about 87.5, 7.1, 5.1, 0.3 percent resp: Gross, Witkop, Biochemistry 4, 2495 (1965). Each of the components A, B, and C consist of 2 chains, one with valine in position 1, comprising 80-95% of the component, and the other with isoleucine in position 1. Structure, characterization, and synthesis of the two isoforms of gramicidin A, N-formylvaline and isoleucine: Sarges, Witkop, J. Am. Chem. Soc. 86, 1862 (1964); 87, 2011, 2020 (1965); Bauer et al., Biochemistry 11, 3266 (1972). Structure of gramicidin B: Sarges, Witkop, J. Am. Chem. Soc. 87, 2027 (1965); of gramicidin C: eidem, Biochemistry 4, 2491 (1965). Synthesis of valine-gramicidin B and C: K. Noda, E. Gross in Chemistry and Biology of Peptides, Proc. 3rd Am. Peptide Symp., J. Meienhofer Ed. (Ann Arbor Science Publishers, Michigan, 1972) pp 241-250. Review: Hunter, Schwartz, "Gramicidins" in Antibiotics I, S. Gottlieb, P. Shaw, Eds. (Springer-Verlag, New York, 1967) pp 642-648. Comprehensive description: G. A. Brewer, Anal. Profiles Drug Subs. 8, 179-218 (1979).
Properties: Spear-shaped or lenticular platelets, mp 229-230°. Almost insol in water (0.6 mg/100 ml). Soluble in the lower alcohols, acetic acid, pyridine. Moderately sol in dry acetone and dioxane. Practically insol in ether, hydrocarbons. Tends to form colloidal suspensions in water.
Melting point: mp 229-230°
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antimicrobial.
Keywords: Antibacterial (Antibiotics); Polypeptides.

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