Tyrocidine
Title: Tyrocidine
CAS Registry Number: 8011-61-8
Literature 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 Type: Hydrochloride mixture
Trademarks: Brevicidin; Rapicidin
Properties: Rods or needles from methanol, dec 240°. [a]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.
Optical Rotation: [a]D20 -101° (c = 1.2 in 95% alc)
 
Derivative Type: Tyrocidine A
CAS Registry Number: 1481-70-5
Molecular Formula: C66H87N13O13
Molecular Weight: 1270.48
Percent Composition: C 62.39%, H 6.90%, N 14.33%, O 16.37%
Literature 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 Type: Tyrocidine A hydrochloride
Properties: Crystals from methanol + water, mp 240-242°. [a]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.
Melting point: mp 240-242°
Optical Rotation: [a]D25 -111° (c = 1.37 in 50% alc)
 
Derivative Type: Tyrocidine B
CAS Registry Number: 865-28-1
Molecular Formula: C68H88N14O13
Molecular Weight: 1309.51
Percent Composition: C 62.37%, H 6.77%, N 14.97%, O 15.88%
Literature 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 Type: Tyrocidine B hydrochloride pentahydrate
Properties: Crystals, mp 236-237°. [a]D-93.0° (c = 0.5 in methanol).
Melting point: mp 236-237°
Optical Rotation: [a]D-93.0° (c = 0.5 in methanol)
 
Derivative Type: Tyrocidine C
CAS Registry Number: 3252-29-7
Molecular Formula: C70H89N15O13
Molecular Weight: 1348.55
Percent Composition: C 62.34%, H 6.65%, N 15.58%, O 15.42%
Literature 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.
 
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.

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