Trocimine | CAS#14368-24-2

MedKoo Cat#: 534880 | Name: Trocimine

Description:

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

Trocimine is a bioactive chemical.

Chemical Structure

Trocimine

CAS#14368-24-2

Theoretical Analysis

MedKoo Cat#: 534880

Name: Trocimine

CAS#: 14368-24-2

Chemical Formula: C17H25NO4

Exact Mass: 307.1784

Molecular Weight: 307.39

Elemental Analysis: C, 66.43; H, 8.20; N, 4.56; O, 20.82

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 #

No Data

Synonym

Trocimine

IUPAC/Chemical Name

Azocine, octahydro-1-(3,4,5-trimethoxybenzoyl)-

InChi Key

WZSDNEJJUSYNSG-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H25NO4/c1-20-14-11-13(12-15(21-2)16(14)22-3)17(19)18-9-7-5-4-6-8-10-18/h11-12H,4-10H2,1-3H3

SMILES Code

O=C(N1CCCCCCC1)C2=CC(OC)=C(OC)C(OC)=C2

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 307.39 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.

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: 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. 3: 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. 4: 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. 5: 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. 6: Mootz HD, Marahiel MA. The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains. J Bacteriol. 1997 Nov;179(21):6843-50. doi: 10.1128/jb.179.21.6843-6850.1997. PMID: 9352938; PMCID: PMC179617. 7: 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. 8: 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. 9: Šprung M, Soldo B, Orhanović S, Bučević-Popović V. Substrate-Induced Conformational Changes of the Tyrocidine Synthetase 1 Adenylation Domain Probed by Intrinsic Trp Fluorescence. Protein J. 2017 Jun;36(3):202-211. doi: 10.1007/s10930-017-9714-1. PMID: 28421413. 10: Samel SA, Czodrowski P, Essen LO. Structure of the epimerization domain of tyrocidine synthetase A. Acta Crystallogr D Biol Crystallogr. 2014 May;70(Pt 5):1442-52. doi: 10.1107/S1399004714004398. Epub 2014 Apr 30. PMID: 24816112. 11: Lee SG, Lipmann F. Tyrocidine synthetase system. Methods Enzymol. 1975;43:585-602. doi: 10.1016/0076-6879(75)43121-4. PMID: 166283. 12: Marques MA, Citron DM, Wang CC. Development of Tyrocidine A analogues with improved antibacterial activity. Bioorg Med Chem. 2007 Nov 1;15(21):6667-77. doi: 10.1016/j.bmc.2007.08.007. Epub 2007 Aug 11. PMID: 17728134; PMCID: PMC2706120. 13: Mukhtar TA, Koteva KP, Wright GD. Chimeric streptogramin-tyrocidine antibiotics that overcome streptogramin resistance. Chem Biol. 2005 Feb;12(2):229-35. doi: 10.1016/j.chembiol.2004.12.009. PMID: 15734650. 14: Yang X, Yousef AE. Antimicrobial peptides produced by Brevibacillus spp.: structure, classification and bioactivity: a mini review. World J Microbiol Biotechnol. 2018 Mar 29;34(4):57. doi: 10.1007/s11274-018-2437-4. PMID: 29594558. 15: Enck S, Kopp F, Marahiel MA, Geyer A. The reversible macrocyclization of Tyrocidine A aldehyde: a hemiaminal reminiscent of the tetrahedral intermediate of macrolactamization. Org Biomol Chem. 2010 Feb 7;8(3):559-63. doi: 10.1039/b917549k. Epub 2009 Nov 27. PMID: 20090972. 16: Morris ME, Jinks-Robertson S. Nucleotide sequence of the LYS2 gene of Saccharomyces cerevisiae: homology to Bacillus brevis tyrocidine synthetase 1. Gene. 1991 Feb 1;98(1):141-5. doi: 10.1016/0378-1119(91)90117-t. PMID: 2013406. 17: Qin C, Bu X, Wu X, Guo Z. A chemical approach to generate molecular diversity based on the scaffold of cyclic decapeptide antibiotic tyrocidine A. J Comb Chem. 2003 Jul-Aug;5(4):353-5. doi: 10.1021/cc0300255. PMID: 12857101. 18: Symons DC, Hodgson B. Isolation and properties of Bacillus brevis mutants unable to produce tyrocidine. J Bacteriol. 1982 Aug;151(2):580-90. PMID: 6284703; PMCID: PMC220298. 19: Bu X, Wu X, Xie G, Guo Z. Synthesis of tyrocidine A and its analogues by spontaneous cyclization in aqueous solution. Org Lett. 2002 Aug 22;4(17):2893-5. doi: 10.1021/ol0263191. PMID: 12182582. 20: Trauger JW, Kohli RM, Mootz HD, Marahiel MA, Walsh CT. Peptide cyclization catalysed by the thioesterase domain of tyrocidine synthetase. Nature. 2000 Sep 14;407(6801):215-8. doi: 10.1038/35025116. PMID: 11001063.