Tyrocidine

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MedKoo CAT#: 462780

CAS#: 8011-61-8

Description: 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. Tyrocidine is the major constituent of tyrothricin, which also contains gramicidin. 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.


Chemical Structure

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Tyrocidine
CAS# 8011-61-8

Theoretical Analysis

MedKoo Cat#: 462780
Name: Tyrocidine
CAS#: 8011-61-8
Chemical Formula: C66H87N13O13
Exact Mass: 1269.6546
Molecular Weight: 1270.5
Elemental Analysis: C, 62.39; H, 6.90; N, 14.33; O, 16.37

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Tyrocidine; Tyrocidines;

IUPAC/Chemical 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

InChi Key: GSXRBRIWJGAPDU-BBVRJQLQSA-N

InChi Code: 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

SMILES Code: CC(C[C@@H]1NC([C@@H](NC([C@H](C(C)C)NC([C@@H](NC([C@@H](NC([C@@H](NC([C@H](NC([C@@H](NC([C@@H]2CCCN2C([C@H](NC1=O)Cc3ccccc3)=O)=O)Cc4ccccc4)=O)Cc5ccccc5)=O)CC(N)=O)=O)CCC(N)=O)=O)Cc6ccc(O)cc6)=O)=O)CCCN)=O)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1270.5 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Juhl DW, van Rensburg W, Bossis X, Vosloo JA, Rautenbach M, Bechinger B. Tyrocidine A interactions with saccharides investigated by CD and NMR spectroscopies. J Pept Sci. 2019 May;25(5):e3163. doi: 10.1002/psc.3163. Epub 2019 Mar 18. PMID: 30884009.

2: Loll PJ, Upton EC, Nahoum V, Economou NJ, Cocklin S. The high resolution structure of tyrocidine A reveals an amphipathic dimer. Biochim Biophys Acta. 2014 May;1838(5):1199-207. doi: 10.1016/j.bbamem.2014.01.033. Epub 2014 Feb 11. PMID: 24530898; PMCID: PMC3980540.

3: Wenzel M, Rautenbach M, Vosloo JA, Siersma T, Aisenbrey CHM, Zaitseva E, Laubscher WE, van Rensburg W, Behrends JC, Bechinger B, Hamoen LW. The Multifaceted Antibacterial Mechanisms of the Pioneering Peptide Antibiotics Tyrocidine and Gramicidin S. mBio. 2018 Oct 9;9(5):e00802-18. doi: 10.1128/mBio.00802-18. PMID: 30301848; PMCID: PMC6178620.

4: Wen G, Qin W, Chen D, Wang Y, Yue X, Liu Z, Cao Y, Du J, Zhou B, Bu X. Stabilizing the monomeric amyloid-β peptide by tyrocidine A prevents and reverses amyloidogenesis without the accumulation of oligomers. Chem Commun (Camb). 2017 Mar 30;53(27):3886-3889. doi: 10.1039/c7cc00506g. PMID: 28317984.

5: Zou Y, Zhao Q, Zhang C, Wang L, Li W, Li X, Wu Q, Hu H. Synthesis and antibacterial activities of novel tyrocidine A glycosylated derivatives towards multidrug-resistant pathogens. J Pept Sci. 2015 Jul;21(7):586-92. doi: 10.1002/psc.2774. Epub 2015 Apr 21. PMID: 25900908.

6: Degen A, Mayerthaler F, Mootz HD, Di Ventura B. Context-dependent activity of A domains in the tyrocidine synthetase. Sci Rep. 2019 Mar 26;9(1):5119. doi: 10.1038/s41598-019-41492-8. PMID: 30914767; PMCID: PMC6435693.

7: Ristow H, Schazschneider B, Vater J, Kleinkauf H. Some characteristics of the DNA-tyrocidine complex and a possible mechanism of the gramicidin action. Biochim Biophys Acta. 1975 Nov 18;414(1):1-8. doi: 10.1016/0005-2787(75)90120-3. PMID: 53075.

8: Cameron AJ, Edwards PJB, Harjes E, Sarojini V. Tyrocidine A Analogues Bearing the Planar d-Phe-2-Abz Turn Motif: How Conformation Impacts Bioactivity. J Med Chem. 2017 Dec 14;60(23):9565-9574. doi: 10.1021/acs.jmedchem.7b00953. Epub 2017 Nov 28. PMID: 29140694.

9: Symons DC, Hodgson B. Isolation and properties of Bacillus brevis mutants unable to produce tyrocidine. J Bacteriol. 1982 Aug;151(2):580-90. doi: 10.1128/JB.151.2.580-590.1982. PMID: 6284703; PMCID: PMC220298.

10: Ristow H, Paulus H. Induction of sporulation in Bacillus brevis. 1. Biochemical events and modulation of RNA synthesis during induction by tyrocidine. Eur J Biochem. 1982 Dec 15;129(2):395-401. doi: 10.1111/j.1432-1033.1982.tb07063.x. PMID: 6185337.