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MedKoo Cat#: 571485 | Name: Mycothiol

Description:

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

Mycothiol is a glyco-inositol-cysteine that conjugates exogenous compounds for detoxication. It is the microbe equivalent of glutathione in the eukaryote, and is acted on by mycothiol disulfide reductase and mycothiol S-conjugate amidase and MDF dehydrogenase. It may be a promising agent against tuberculosis as an important cellcular antioxidant.

Chemical Structure

Mycothiol
Mycothiol
CAS#192126-76-4

Theoretical Analysis

MedKoo Cat#: 571485

Name: Mycothiol

CAS#: 192126-76-4

Chemical Formula: C17H30N2O12S

Exact Mass: 486.1519

Molecular Weight: 486.49

Elemental Analysis: C, 41.97; H, 6.22; N, 5.76; O, 39.46; S, 6.59

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
Mycothiol
IUPAC/Chemical Name
(R)-2-acetamido-N-((2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3-yl)-3-mercaptopropanamide
InChi Key
MQBCDKMPXVYCGO-FQBKTPCVSA-N
InChi Code
InChI=1S/C17H30N2O12S/c1-4(21)18-5(3-32)16(29)19-7-9(23)8(22)6(2-20)30-17(7)31-15-13(27)11(25)10(24)12(26)14(15)28/h5-15,17,20,22-28,32H,2-3H2,1H3,(H,18,21)(H,19,29)/t5-,6+,7+,8+,9+,10-,11-,12+,13+,14+,15-,17+/m0/s1
SMILES Code
CC(N[C@H](C(N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]2[C@H](O)[C@H](O)[C@@H](O)[C@H](O)[C@H]2O)=O)CS)=O
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
>2 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 486.49 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: Hugo M, Van Laer K, Reyes AM, Vertommen D, Messens J, Radi R, Trujillo M. Mycothiol/mycoredoxin 1-dependent reduction of the peroxiredoxin AhpE from Mycobacterium tuberculosis. J Biol Chem. 2014 Feb 21;289(8):5228-39. doi: 10.1074/jbc.M113.510248. Epub 2013 Dec 30. PubMed PMID: 24379404; PubMed Central PMCID: PMC3931079. 2: Riordan SW, Field JJ, Corkran HM, Dasyam N, Stocker BL, Timmer MS, Harvey JE, Teesdale-Spittle PH. Synthesis of mycothiol conjugate analogues and evaluation of their antimycobacterial activity. Bioorg Med Chem Lett. 2015;25(10):2152-5. doi: 10.1016/j.bmcl.2015.03.070. Epub 2015 Mar 31. PubMed PMID: 25881831. 3: Nilewar SS, Kathiravan MK. Mycothiol: a promising antitubercular target. Bioorg Chem. 2014 Feb;52:62-8. doi: 10.1016/j.bioorg.2013.11.004. Epub 2013 Nov 21. Review. PubMed PMID: 24368170. 4: Pedre B, Van Molle I, Villadangos AF, Wahni K, Vertommen D, Turell L, Erdogan H, Mateos LM, Messens J. The Corynebacterium glutamicum mycothiol peroxidase is a reactive oxygen species-scavenging enzyme that shows promiscuity in thiol redox control. Mol Microbiol. 2015 Jun;96(6):1176-91. doi: 10.1111/mmi.12998. Epub 2015 Apr 11. PubMed PMID: 25766783. 5: Manabe S, Ito Y. Mycothiol synthesis by an anomerization reaction through endocyclic cleavage. Beilstein J Org Chem. 2016 Feb 22;12:328-33. doi: 10.3762/bjoc.12.35. eCollection 2016. PubMed PMID: 26977192; PubMed Central PMCID: PMC4778527. 6: Si M, Zhao C, Zhang B, Wei D, Chen K, Yang X, Xiao H, Shen X. Overexpression of Mycothiol Disulfide Reductase Enhances Corynebacterium glutamicum Robustness by Modulating Cellular Redox Homeostasis and Antioxidant Proteins under Oxidative Stress. Sci Rep. 2016 Jul 7;6:29491. doi: 10.1038/srep29491. PubMed PMID: 27383057; PubMed Central PMCID: PMC4935862. 7: Si M, Xu Y, Wang T, Long M, Ding W, Chen C, Guan X, Liu Y, Wang Y, Shen X, Liu SJ. Functional characterization of a mycothiol peroxidase in Corynebacterium glutamicum that uses both mycoredoxin and thioredoxin reducing systems in the response to oxidative stress. Biochem J. 2015 Jul 1;469(1):45-57. doi: 10.1042/BJ20141080. Epub 2015 Apr 20. PubMed PMID: 25891483. 8: Kocabas E, Liu H, Hernick M. Identity of cofactor bound to mycothiol conjugate amidase (Mca) influenced by expression and purification conditions. Biometals. 2015 Aug;28(4):755-63. doi: 10.1007/s10534-015-9864-6. Epub 2015 Jun 5. PubMed PMID: 26044118. 9: Tossounian MA, Pedre B, Wahni K, Erdogan H, Vertommen D, Van Molle I, Messens J. Corynebacterium diphtheriae methionine sulfoxide reductase a exploits a unique mycothiol redox relay mechanism. J Biol Chem. 2015 May 1;290(18):11365-75. doi: 10.1074/jbc.M114.632596. Epub 2015 Mar 9. PubMed PMID: 25752606; PubMed Central PMCID: PMC4416841. 10: Hernick M. Mycothiol: a target for potentiation of rifampin and other antibiotics against Mycobacterium tuberculosis. Expert Rev Anti Infect Ther. 2013 Jan;11(1):49-67. doi: 10.1586/eri.12.152. Review. PubMed PMID: 23428102. 11: Bhaskar A, Chawla M, Mehta M, Parikh P, Chandra P, Bhave D, Kumar D, Carroll KS, Singh A. Reengineering redox sensitive GFP to measure mycothiol redox potential of Mycobacterium tuberculosis during infection. PLoS Pathog. 2014 Jan 30;10(1):e1003902. doi: 10.1371/journal.ppat.1003902. eCollection 2014 Jan. PubMed PMID: 24497832; PubMed Central PMCID: PMC3907381. 12: Liu YB, Chen C, Chaudhry MT, Si MR, Zhang L, Wang Y, Shen XH. Enhancing Corynebacterium glutamicum robustness by over-expressing a gene, mshA, for mycothiol glycosyltransferase. Biotechnol Lett. 2014 Jul;36(7):1453-9. doi: 10.1007/s10529-014-1501-x. Epub 2014 Apr 16. PubMed PMID: 24737070. 13: Lessmeier L, Hoefener M, Wendisch VF. Formaldehyde degradation in Corynebacterium glutamicum involves acetaldehyde dehydrogenase and mycothiol-dependent formaldehyde dehydrogenase. Microbiology. 2013 Dec;159(Pt 12):2651-62. doi: 10.1099/mic.0.072413-0. Epub 2013 Sep 24. PubMed PMID: 24065717. 14: Janata J, Kadlcik S, Koberska M, Ulanova D, Kamenik Z, Novak P, Kopecky J, Novotna J, Radojevic B, Plhackova K, Gazak R, Najmanova L. Lincosamide synthetase--a unique condensation system combining elements of nonribosomal peptide synthetase and mycothiol metabolism. PLoS One. 2015 Mar 5;10(3):e0118850. doi: 10.1371/journal.pone.0118850. eCollection 2015. PubMed PMID: 25741696; PubMed Central PMCID: PMC4351081. 15: Vargas D, Hageman S, Gulati M, Nobile CJ, Rawat M. S-nitrosomycothiol reductase and mycothiol are required for survival under aldehyde stress and biofilm formation in Mycobacterium smegmatis. IUBMB Life. 2016 Aug;68(8):621-8. doi: 10.1002/iub.1524. Epub 2016 Jun 19. PubMed PMID: 27321674; PubMed Central PMCID: PMC5538257. 16: Si M, Long M, Chaudhry MT, Xu Y, Zhang P, Zhang L, Shen X. Functional characterization of Corynebacterium glutamicum mycothiol S-conjugate amidase. PLoS One. 2014 Dec 16;9(12):e115075. doi: 10.1371/journal.pone.0115075. eCollection 2014. PubMed PMID: 25514023; PubMed Central PMCID: PMC4267739. 17: Sharma SV, Van Laer K, Messens J, Hamilton CJ. Thiol Redox and pKa Properties of Mycothiol, the Predominant Low-Molecular-Weight Thiol Cofactor in the Actinomycetes. Chembiochem. 2016 Sep 15;17(18):1689-92. doi: 10.1002/cbic.201600228. Epub 2016 Jul 28. PubMed PMID: 27332744. 18: Liu YB, Long MX, Yin YJ, Si MR, Zhang L, Lu ZQ, Wang Y, Shen XH. Physiological roles of mycothiol in detoxification and tolerance to multiple poisonous chemicals in Corynebacterium glutamicum. Arch Microbiol. 2013 Jun;195(6):419-29. doi: 10.1007/s00203-013-0889-3. Epub 2013 Apr 25. PubMed PMID: 23615850. 19: Newton GL, Leung SS, Wakabayashi JI, Rawat M, Fahey RC. The DinB superfamily includes novel mycothiol, bacillithiol, and glutathione S-transferases. Biochemistry. 2011 Dec 13;50(49):10751-60. doi: 10.1021/bi201460j. Epub 2011 Nov 17. PubMed PMID: 22059487; PubMed Central PMCID: PMC3232311. 20: Wang T, Gao F, Kang Y, Zhao C, Su T, Li M, Si M, Shen X. Mycothiol peroxidase MPx protects Corynebacterium glutamicum against acid stress by scavenging ROS. Biotechnol Lett. 2016 Jul;38(7):1221-8. doi: 10.1007/s10529-016-2099-y. Epub 2016 Apr 6. PubMed PMID: 27053080.

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