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MedKoo Cat#: 462590 | Name: Viomycin (free base)

Description:

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

Viomycin (free base) is a tuberactinomycin antibiotic essential for treating multidrug-resistant tuberculosis. It inhibits bacterial protein synthesis by blocking elongation factor G (EF-G) catalyzed translocation of messenger RNA on the ribosome.

Chemical Structure

Viomycin (free base)
Viomycin (free base)
CAS#32988-50-4 (free base)

Theoretical Analysis

MedKoo Cat#: 462590

Name: Viomycin (free base)

CAS#: 32988-50-4 (free base)

Chemical Formula: C25H43N13O10

Exact Mass: 685.3256

Molecular Weight: 685.70

Elemental Analysis: C, 43.79; H, 6.32; N, 26.56; O, 23.33

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 #
32988-50-4 (free base); 37883-00-4 (sulfate)
Synonym
Viomycin (free base); Celiomycin; Floromycin; Viocin
IUPAC/Chemical Name
(S)-3,6-diamino-N-((3S,9S,12S,15S,Z)-3-((4R,6S)-6-hydroxy-2-iminohexahydropyrimidin-4-yl)-9,12-bis(hydroxymethyl)-2,5,8,11,14-pentaoxo-6-(ureidomethylene)-1,4,7,10,13-pentaazacyclohexadecan-15-yl)hexanamide
InChi Key
GXFAIFRPOKBQRV-GHXCTMGLSA-N
InChi Code
InChI=1S/C25H43N13O10/c26-3-1-2-10(27)4-16(41)32-12-6-30-23(47)18(11-5-17(42)37-24(28)36-11)38-20(44)13(7-31-25(29)48)33-21(45)14(8-39)35-22(46)15(9-40)34-19(12)43/h7,10-12,14-15,17-18,39-40,42H,1-6,8-9,26-27H2,(H,30,47)(H,32,41)(H,33,45)(H,34,43)(H,35,46)(H,38,44)(H3,28,36,37)(H3,29,31,48)/b13-7-/t10-,11+,12-,14-,15-,17-,18-/m0/s1
SMILES Code
NCCC[C@@H](CC(N[C@H]1CNC([C@H]([C@H]2C[C@@H](NC(N2)=N)O)NC(/C(NC([C@@H](NC([C@@H](NC1=O)CO)=O)CO)=O)=C/NC(N)=O)=O)=O)=O)N
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 685.70 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: Holm M, Borg A, Ehrenberg M, Sanyal S. Molecular mechanism of viomycin inhibition of peptide elongation in bacteria. Proc Natl Acad Sci U S A. 2016 Jan 26;113(4):978-83. doi: 10.1073/pnas.1517541113. Epub 2016 Jan 11. PMID: 26755601; PMCID: PMC4743798. 2: Holm M, Mandava CS, Ehrenberg M, Sanyal S. The mechanism of error induction by the antibiotic viomycin provides insight into the fidelity mechanism of translation. Elife. 2019 Jun 7;8:e46124. doi: 10.7554/eLife.46124. PMID: 31172942; PMCID: PMC6594751. 3: VIOMYCIN. Br Med J. 1954 Feb 13;1(4858):384-5. PMID: 13115734. 4: TAKEDA K. [Viomycin]. J Antibiot B. 1962 Apr;15:68-73. Japanese. PMID: 14039625. 5: Barkei JJ, Kevany BM, Felnagle EA, Thomas MG. Investigations into viomycin biosynthesis by using heterologous production in Streptomyces lividans. Chembiochem. 2009 Jan 26;10(2):366-76. doi: 10.1002/cbic.200800646. PMID: 19105177; PMCID: PMC2765823. 6: Stokowa-Sołtys K, Barbosa NA, Kasprowicz A, Wieczorek R, Gaggelli N, Gaggelli E, Valensin G, Wrzesiński J, Ciesiołka J, Kuliński T, Szczepanik W, Jeżowska- Bojczuk M. Studies of viomycin, an anti-tuberculosis antibiotic: copper(ii) coordination, DNA degradation and the impact on delta ribozyme cleavage activity. Dalton Trans. 2016 May 17;45(20):8645-58. doi: 10.1039/c6dt00245e. PMID: 27143296. 7: Ermolenko DN, Spiegel PC, Majumdar ZK, Hickerson RP, Clegg RM, Noller HF. The antibiotic viomycin traps the ribosome in an intermediate state of translocation. Nat Struct Mol Biol. 2007 Jun;14(6):493-7. doi: 10.1038/nsmb1243. Epub 2007 May 21. PMID: 17515906. 8: Kitagawa T, Fujitake T, Taniyama H, Aikawa T. Enzyme immunoassay of viomycin. New cross-linking reagent for enzyme labelling and a preparation method for antiserum to viomycin. J Biochem. 1978 May;83(5):1493-501. doi: 10.1093/oxfordjournals.jbchem.a132059. PMID: 207686. 9: Wallis MG, Streicher B, Wank H, von Ahsen U, Clodi E, Wallace ST, Famulok M, Schroeder R. In vitro selection of a viomycin-binding RNA pseudoknot. Chem Biol. 1997 May;4(5):357-66. doi: 10.1016/s1074-5521(97)90126-5. PMID: 9195872. 10: VIOMICINA [Viomycin]. Clin Nuova Rass Prog Med Int. 1951 Sep 22-9;13(12-13):361-2. Undetermined Language. PMID: 14936260. 11: Lechowski L. Viomycin. Tetrahedron Lett. 1969 Feb;(6):479-82. doi: 10.1016/s0040-4039(01)87723-6. PMID: 4307473. 12: ANGIONI G. La viomicina [Viomycin]. Rass Med Sarda. 1951 Mar- Apr;2(3-4):76-8. Undetermined Language. PMID: 14854253. 13: Akbergenov R, Shcherbakov D, Matt T, Duscha S, Meyer M, Wilson DN, Böttger EC. Molecular basis for the selectivity of antituberculosis compounds capreomycin and viomycin. Antimicrob Agents Chemother. 2011 Oct;55(10):4712-7. doi: 10.1128/AAC.00628-11. Epub 2011 Jul 18. PMID: 21768509; PMCID: PMC3187005. 14: Stanley RE, Blaha G, Grodzicki RL, Strickler MD, Steitz TA. The structures of the anti-tuberculosis antibiotics viomycin and capreomycin bound to the 70S ribosome. Nat Struct Mol Biol. 2010 Mar;17(3):289-93. doi: 10.1038/nsmb.1755. Epub 2010 Feb 14. PMID: 20154709; PMCID: PMC2917106. 15: Kitagawa T, Tanimori H, Yoshida K, Miura T, Fujiwara K. High dimensional structure of the antigen-binding site of anti-viomycin immunoglobulin analyzed by enzyme immunoassay. J Biochem. 1982 May;91(5):1601-5. doi: 10.1093/oxfordjournals.jbchem.a133851. PMID: 6284729. 16: Bloudoff K, Schmeing TM. Crystallization and preliminary crystallographic analysis of the first condensation domain of viomycin synthetase. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 Apr 1;69(Pt 4):412-5. doi: 10.1107/S1744309113004004. Epub 2013 Mar 28. PMID: 23545648; PMCID: PMC3614167. 17: Fei X, Yin X, Zhang L, Zabriskie TM. Roles of VioG and VioQ in the incorporation and modification of the Capreomycidine residue in the peptide antibiotic viomycin. J Nat Prod. 2007 Apr;70(4):618-22. doi: 10.1021/np060605u. Epub 2007 Feb 16. PMID: 17302456; PMCID: PMC2825577. 18: LEVADITI C, VAISMAN A, HENRY-EVENO J, CHAIGNEAU-ERHARD H. La viomycine, nouvel antibiotique tuberculostatique [Viomycin, a new tuberculostatic antibiotic]. Rev Immunol Ther Antimicrob. 1951;15(5-6):298-320. Undetermined Language. PMID: 14942194. 19: Wank H, Clodi E, Wallis MG, Schroeder R. The antibiotic viomycin as a model peptide for the origin of the co-evolution of RNA and proteins. Orig Life Evol Biosph. 1999 Aug;29(4):391-404. doi: 10.1023/a:1006572028643. PMID: 10472628. 20: Skinner RH, Cundliffe E. Resistance to the antibiotics viomycin and capreomycin in the Streptomyces species which produce them. J Gen Microbiol. 1980 Sep;120(1):95-104. doi: 10.1099/00221287-120-1-95. PMID: 6163840.