# Mycothiol
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Mycothiol
> Markdown URL: https://mediated.wiki/source/Mycothiol.md
> Source: https://en.wikipedia.org/wiki/Mycothiol
> Source revision: 1335306539
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 433271578
| ImageFileL1 = Mycothiol structure.png
| ImageSizeL1 = 125px
| ImageFileR1 = Mycothiol ball and stick.png
| ImageSizeR1 = 125px
| ImageFile2 = Mycothiol spacefill.png
| ImageSize2 = 150px
|IUPACName=(2''R'')-2-acetamido-''N''-[(2''R'',3''R'',4''R'',5''S'',6''R'')-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2''R'',3''S'',5''R'',6''R'')-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]-3-sulfanylpropanamide
|OtherNames=Mycothiol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=192126-76-4
| PubChem=441148
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 16768
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 10193006
| SMILES = CC(=O)N[C@@H](CS)C(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1O[C@@H]2[C@@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)O)O)O)CO)O)O
| InChI = 1/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
| InChIKey = MQBCDKMPXVYCGO-FQBKTPCVBG
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = MQBCDKMPXVYCGO-FQBKTPCVSA-N
| RTECS =
| MeSHName =
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C06717
}}
|Section2={{Chembox Properties
| C = 17 | H = 30 | N = 2 | O = 12 | S = 1
}}
}}
'''Mycothiol''' (MSH or AcCys-GlcN-Ins) is an unusual [thiol](/source/thiol) compound found in the [Actinomycetota](/source/Actinomycetota).[{{cite journal |author=Fahey RC |title=Novel thiols of prokaryotes |journal=Annu. Rev. Microbiol. |volume=55 |pages=333–56 |year=2001 |pmid=11544359 |doi=10.1146/annurev.micro.55.1.333}}][Jothivasan VK, Hamilton CJ, (2008) Mycothiol: synthesis, biosynthesis and biological functions of the major low molecular weight thiol in actinomycetes. Natural Product Reports, (25). 1091-1117 [https://dx.doi.org/10.1039/b616489g]] It is composed of a [cysteine](/source/cysteine) residue with an acetylated amino group linked to [glucosamine](/source/glucosamine), which is then linked to [inositol](/source/inositol).[{{cite journal |vauthors=Newton GL, Buchmeier N, Fahey RC |title=Biosynthesis and functions of mycothiol, the unique protective thiol of Actinobacteria |journal=Microbiol. Mol. Biol. Rev. |volume=72 |issue=3 |pages=471–94 |date=September 2008 |pmid=18772286 |doi=10.1128/MMBR.00008-08 |pmc=2546866}}] The oxidized, [disulfide](/source/disulfide) form of mycothiol (MSSM) is called mycothione, and is reduced to mycothiol by the [flavoprotein](/source/flavoprotein) [mycothione reductase](/source/mycothione_reductase).[{{cite journal |vauthors=Patel MP, Blanchard JS |title=Expression, purification, and characterization of Mycobacterium tuberculosis mycothione reductase |journal=Biochemistry |volume=38 |issue=36 |pages=11827–33 |date=September 1999 |pmid=10512639 |doi=10.1021/bi991025h}}][{{cite journal |vauthors=Patel MP, Blanchard JS |title=Mycobacterium tuberculosis mycothione reductase: pH dependence of the kinetic parameters and kinetic isotope effects |journal=Biochemistry |volume=40 |issue=17 |pages=5119–26 |date=May 2001 |pmid=11318633 |doi=10.1021/bi0029144}}] Mycothiol biosynthesis and mycothiol-dependent enzymes such as [mycothiol-dependent formaldehyde dehydrogenase](/source/mycothiol-dependent_formaldehyde_dehydrogenase) and mycothione reductase have been proposed to be good [drug target](/source/drug_target)s for the development of treatments for [tuberculosis](/source/tuberculosis).[{{cite journal |vauthors=Rawat M, Av-Gay Y |title=Mycothiol-dependent proteins in actinomycetes |journal=FEMS Microbiol. Rev. |volume=31 |issue=3 |pages=278–92 |date=April 2007 |pmid=17286835 |doi=10.1111/j.1574-6976.2006.00062.x|doi-access=free }}][{{cite journal |vauthors=Newton GL, Fahey RC |title=Mycothiol biochemistry |journal=Arch. Microbiol. |volume=178 |issue=6 |pages=388–94 |date=December 2002 |pmid=12420157 |doi=10.1007/s00203-002-0469-4|bibcode=2002ArMic.178..388N |s2cid=23893254 }}]
== See also ==
* [Glutathione](/source/Glutathione), analogous function in other bacteria
* [Bacillithiol](/source/Bacillithiol)
== References ==
{{reflist}}
== External links ==
*[https://archive.today/20121224172559/http://web.uct.ac.za/depts/chempath/pathogens.htm The Biochemistry of Pathogens: The metabolism and function of mycothiol in the mycobacteria.]
Category:Thiols
Category:Acetamides
Category:Propionamides
Category:Tetrahydropyrans
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Adapted from the Wikipedia article [Mycothiol](https://en.wikipedia.org/wiki/Mycothiol) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Mycothiol?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.