Mycothiol

Quality 0.50 · 2 views · Updated 2 months ago

title: "Mycothiol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["thiols", "acetamides", "propionamides", "tetrahydropyrans"] topic_path: "general/thiols" source: "https://en.wikipedia.org/wiki/Mycothiol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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=(2R)-2-acetamido-N-[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(2R,3S,5R,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyoxan-3-yl]-3-sulfanylpropanamide |OtherNames=Mycothiol |Section1={{Chembox Identifiers | CASNo_Ref = | CASNo=192126-76-4 | PubChem=441148 | ChEBI_Ref = | ChEBI = 16768 | ChemSpiderID_Ref = | ChemSpiderID = 10193006 | SMILES = CC(=O)NC@@HC(=O)N[C@@H]1C@HO | 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 = | 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 = | StdInChIKey = MQBCDKMPXVYCGO-FQBKTPCVSA-N | RTECS = | MeSHName = | KEGG_Ref = | 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 compound found in the Actinomycetota. It is composed of a cysteine residue with an acetylated amino group linked to glucosamine, which is then linked to inositol. The oxidized, disulfide form of mycothiol (MSSM) is called mycothione, and is reduced to mycothiol by the flavoprotein mycothione reductase. Mycothiol biosynthesis and mycothiol-dependent enzymes such as mycothiol-dependent formaldehyde dehydrogenase and mycothione reductase have been proposed to be good drug targets for the development of treatments for tuberculosis.

References

References

  1. Fahey RC. (2001). "Novel thiols of prokaryotes". Annu. Rev. Microbiol..
  2. 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]
  3. (September 2008). "Biosynthesis and functions of mycothiol, the unique protective thiol of Actinobacteria". Microbiol. Mol. Biol. Rev..
  4. (September 1999). "Expression, purification, and characterization of Mycobacterium tuberculosis mycothione reductase". Biochemistry.
  5. (May 2001). "Mycobacterium tuberculosis mycothione reductase: pH dependence of the kinetic parameters and kinetic isotope effects". Biochemistry.
  6. (April 2007). "Mycothiol-dependent proteins in actinomycetes". FEMS Microbiol. Rev..
  7. (December 2002). "Mycothiol biochemistry". Arch. Microbiol..

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

thiolsacetamidespropionamidestetrahydropyrans