9836. Tyrocidine
Nomenclature
Description and references
Peptide antibiotic mixture produced by Bacillus brevis: major constituent of tyrothricin, q.v. Isoln: Hotchkiss et al., J. Biol. Chem. 141, 155, 163 (1941); Moses, US 3265572 (1966 to Penick). Separated into the three components, tyrocidines A, B, and C. Review of chemistry and biosynthesis: E. Katz, A. L. Demain, Bacteriol. Rev. 41, 449-474 (1977). Regulatory role in bacterial sporogenesis: H. Ristow et al., Nature 280, 165 (1979); eidem, Eur. J. Biochem. 129, 395 (1982); W. Pschorn et al., ibid. 403. Structure-activity relationship: W. Danders et al., Antimicrob. Agents Chemother. 22, 785 (1982).
Derivative
Hydrochloride mixture.Nomenclature
Brevicidin; Rapicidin.Properties
Rods or needles from methanol, dec 240°. [α]D20 101° (c = 1.2 in 95% alc). Soluble in 95% alc, acetic acid, pyridine; slightly sol in water, acetone, abs alcohol. Practically insol in ether, chloroform, hydrocarbons.Derivative
Tyrocidine A.Nomenclature
Description and references
Separation from the tyrocidine mixture: Battersby, Craig, J. Am. Chem. Soc. 74, 4019, 4023 (1952). Structure: Paladine, Craig, ibid. 76, 688 (1954). Synthesis: Ohno et al., Bull. Chem. Soc. Jpn. 39, 1738 (1966); K. Okamoto et al., ibid. 50, 231 (1977).
Derivative
Tyrocidine A hydrochloride.Properties
Crystals from methanol + water, mp 240-242°. [α]D25 111° (c = 1.37 in 50% alc). Freely sol in aq methanol or alc; slightly sol in methanol, ethanol. Practically insol in chloroform, acetone, ether.Derivative
Tyrocidine B.Nomenclature
Description and references
Purification and amino acid sequence determination: King, Craig, J. Am. Chem. Soc. 77, 6624, 6627 (1955). Synthesis: Kuromizu, Izumiya, Experientia 26, 587 (1970). Possesses the same structure as tyrocidine A except that l-tryptophan replaces the l-phenylalanine.
Properties
Crystals from methanol + isopropyl ether.Derivative
Tyrocidine B hydrochloride pentahydrate.Properties
Crystals, mp 236-237°. [α]D93.0° (c = 0.5 in methanol).Derivative
Tyrocidine C.Nomenclature
Description and references
Separation from the tyrocidine mixture: Ruttenberg et al., Biochemistry 4, 11 (1965). Possesses same structure as tyrocidine B except that d-tryptophan replaces d-phenylalanine attached to l-asparagine. Synthesis: Kuromizu, Izumiya, Tetrahedron Lett. 1970, 1471.
Therapeutic Category
Antibacterial.
Keywords
Antibacterial (Antibiotics); Polypeptides