Tyrocidine

Tyrocidine
Names
	IUPAC name 3-((3S,6R,9S,12S,15S, 18S,21S,24S,27R,32aS) -9-(2-amino-2-oxoethyl)- 21-(3-aminopropyl)- 3,6,27-tribenzyl-15- (4-hydroxybenzyl)-24-isobutyl- 18-isopropyl- 1,4,7,10,13,16,19,22,25,28- decaoxodotriacontahydropyrrolo[1,2-a] [1,4,7,10,13,16,19,22,25,28] decaazacyclotriacontin- 12-yl)propanamide
Identifiers
CAS Number	8011-61-8 ; A: 1481-70-5 ; B: 865-28-1 ; C: 3252-29-7 ;
3D model (JSmol)	A: Interactive image;
ChEBI	A: CHEBI:29701;
ChEMBL	A: ChEMBL408504;
ChemSpider	A: 17286446; B: 24631547; C: 24640331; D: 28533724;
EC Number	232-375-3;
KEGG	A: C12041;
PubChem CID	A: 16129635;
UNII	0XQ8A2PG8K ; A: V134656H89;
	InChI A: InChI=1S/C66H87N13O13/c1-38(2)32-47-59(85)77-52(36-42-20-12-7-13-21-42)66(92)79-31-15-23-53(79)64(90)76-49(34-41-18-10-6-11-19-41)61(87)74-48(33-40-16-8-5-9-17-40)60(86)75-51(37-55(69)82)62(88)70-46(28-29-54(68)81)58(84)73-50(35-43-24-26-44(80)27-25-43)63(89)78-56(39(3)4)65(91)71-45(22-14-30-67)57(83)72-47/h5-13,16-21,24-27,38-39,45-53,56,80H,14-15,22-23,28-37,67H2,1-4H3,(H2,68,81)(H2,69,82)(H,70,88)(H,71,91)(H,72,83)(H,73,84)(H,74,87)(H,75,86)(H,76,90)(H,77,85)(H,78,89)/t45-,46-,47-,48+,49-,50-,51-,52+,53-,56-/m0/s1 Key: GSXRBRIWJGAPDU-BBVRJQLQSA-N Computed by InChI 1.0.6 (PubChem release 2021.10.14);
	SMILES A: CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)CC3=CC=C(C=C3)O)CCC(=O)N)CC(=O)N)CC4=CC=CC=C4)CC5=CC=CC=C5)CC6=CC=CC=C6;
Properties
Chemical formula	C66H87N13O13
Molar mass	1270.47628
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Tyrocidine is a mixture of cyclic decapeptides produced by the bacteria Brevibacillus 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.

^ Pubchem: Tyrocidine and Tyrothricin."PubChem Compound Result".
^ Mootz HD, Marahiel MA (November 1997). "The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains". J. Bacteriol. 179 (21): 6843–50. doi:10.1128/jb.179.21.6843-6850.1997. PMC 179617. PMID 9352938.

[pcid16129635-1] Pubchem: Tyrocidine and Tyrothricin."PubChem Compound Result".

[pmid9352938-2] Mootz HD, Marahiel MA (November 1997). "The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains". J. Bacteriol. 179 (21): 6843–50. doi:10.1128/jb.179.21.6843-6850.1997. PMC 179617. PMID 9352938.

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