MedKoo Cat#: 462780 | Name: Tyrocidine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Tyrocidine
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: 1270.50

Elemental Analysis: C, 62.39; H, 6.90; N, 14.33; O, 16.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 1,270.50 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
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.