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.
Tyropanoate Sodium Tyrosinase Tyrosine Tyrothricin Yam, Mexican

Tyrocidine
Tyrocidine A.svg
Identifiers
CAS number 8011-61-8 YesY
PubChem 16129635
Properties
Molecular formula C66H87N13O13
Molar mass 1270.47628
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Tyrocidine is a mixture of cyclic decapeptides produced by the bacteria Bacillus brevis found in soil. It can be composed of 4 different amino acid sequences, giving tyrocidine A–D (See figure 1). Tyrocidine is the major constituent of tyrothricin, which also contains gramicidin.[1] Tyrocidine was the first commercially available antibiotic, but has been found to be toxic toward human blood and reproductive cells. The function of tyrocidine within its host B. brevis is thought to be regulation of sporulation.[2]

Figure 1: a) Amino acid sequence of tyrocidine A. b) Sequence changes for the 4 types of tyrocidine.

Tyrocidines A, B, and C are cyclic decapeptides. The biosynthesis of tyrocidine involves three enzymes. Parts of its sequence are identical to gramicidin S.