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'''Mycothiol''' (MSH or AcCys-GlcN-Ins) is an unusual ] compound found in the ].<ref>{{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}}</ref><ref>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 </ref> It is composed of a ] residue with an acetylated amino group linked to ], which is then linked to ].<ref>{{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}}</ref> The oxidized, ] form of mycothiol (MSSM) is called mycothione, and is reduced to mycothiol by the ] ].<ref>{{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}}</ref><ref>{{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}}</ref> Mycothiol biosynthesis and mycothiol-dependent enzymes such as ] and mycothione reductase have been proposed to be good ]s for the development of treatments for ].<ref>{{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 }}</ref><ref>{{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}}</ref> '''Mycothiol''' (MSH or AcCys-GlcN-Ins) is an unusual ] compound found in the ].<ref>{{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}}</ref><ref>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 </ref> It is composed of a ] residue with an acetylated amino group linked to ], which is then linked to ].<ref>{{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}}</ref> The oxidized, ] form of mycothiol (MSSM) is called mycothione, and is reduced to mycothiol by the ] ].<ref>{{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}}</ref><ref>{{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}}</ref> Mycothiol biosynthesis and mycothiol-dependent enzymes such as ] and mycothione reductase have been proposed to be good ]s for the development of treatments for ].<ref>{{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 }}</ref><ref>{{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|s2cid=23893254 }}</ref>


== See also == == See also ==

Latest revision as of 22:15, 3 October 2022

Mycothiol
Names
IUPAC name (2R)-2-acetamido-N-oxyoxan-3-yl]-3-sulfanylpropanamide
Other names Mycothiol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: MQBCDKMPXVYCGO-FQBKTPCVSA-N
  • 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/s1Key: MQBCDKMPXVYCGO-FQBKTPCVBG
SMILES
  • CC(=O)N(CS)C(=O)N1(((O1O2((((2O)O)O)O)O)CO)O)O
Properties
Chemical formula C17H30N2O12S
Molar mass 486.49 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

See also

References

  1. Fahey RC (2001). "Novel thiols of prokaryotes". Annu. Rev. Microbiol. 55: 333–56. doi:10.1146/annurev.micro.55.1.333. PMID 11544359.
  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
  3. Newton GL, Buchmeier N, Fahey RC (September 2008). "Biosynthesis and functions of mycothiol, the unique protective thiol of Actinobacteria". Microbiol. Mol. Biol. Rev. 72 (3): 471–94. doi:10.1128/MMBR.00008-08. PMC 2546866. PMID 18772286.
  4. Patel MP, Blanchard JS (September 1999). "Expression, purification, and characterization of Mycobacterium tuberculosis mycothione reductase". Biochemistry. 38 (36): 11827–33. doi:10.1021/bi991025h. PMID 10512639.
  5. Patel MP, Blanchard JS (May 2001). "Mycobacterium tuberculosis mycothione reductase: pH dependence of the kinetic parameters and kinetic isotope effects". Biochemistry. 40 (17): 5119–26. doi:10.1021/bi0029144. PMID 11318633.
  6. Rawat M, Av-Gay Y (April 2007). "Mycothiol-dependent proteins in actinomycetes". FEMS Microbiol. Rev. 31 (3): 278–92. doi:10.1111/j.1574-6976.2006.00062.x. PMID 17286835.
  7. Newton GL, Fahey RC (December 2002). "Mycothiol biochemistry". Arch. Microbiol. 178 (6): 388–94. doi:10.1007/s00203-002-0469-4. PMID 12420157. S2CID 23893254.

Mycobacterium tuberculosis is extraordinarily sensitive to killing by a vitamin C-induced Fenton reaction Published 21 May 2013. Nature Communications4, Article number:1881 doi:10.1038/ncomms2898

External links

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