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Latest revision as of 22:15, 3 October 2022 edit undoCitation bot (talk | contribs)Bots5,450,456 edits Add: s2cid. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Thiols | #UCB_Category 40/83 |
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{{chembox |
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{{chembox |
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| verifiedrevid = 366457771 |
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| verifiedrevid = 433271578 |
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| ImageFileL1 = Mycothiol structure.png |
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| ImageFileL1 = Mycothiol structure.png |
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| ImageSizeL1 = 125px |
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| ImageSizeL1 = 125px |
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|OtherNames=Mycothiol |
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|OtherNames=Mycothiol |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=192126-76-4 |
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| CASNo=192126-76-4 |
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| PubChem=441148 |
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| PubChem=441148 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| SMILES=CC(=O)N(CS)C(=O)N1(((O1OC2((C((2O)O)O)O)O)CO)O)O |
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| ChEBI = 16768 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 10193006 |
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| SMILES = CC(=O)N(CS)C(=O)N1(((O1O2((((2O)O)O)O)O)CO)O)O |
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| 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 |
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| InChIKey = MQBCDKMPXVYCGO-FQBKTPCVBG |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = MQBCDKMPXVYCGO-FQBKTPCVSA-N |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C06717 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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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 |issue= |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 |author=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 |year=2008 |month=September |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 |author=Patel MP, Blanchard JS |title=Expression, purification, and characterization of Mycobacterium tuberculosis mycothione reductase |journal=Biochemistry |volume=38 |issue=36 |pages=11827–33 |year=1999 |month=September |pmid=10512639 |doi=10.1021/bi991025h}}</ref><ref>{{cite journal |author=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 |year=2001 |month=May |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 |author=Rawat M, Av-Gay Y |title=Mycothiol-dependent proteins in actinomycetes |journal=FEMS Microbiol. Rev. |volume=31 |issue=3 |pages=278–92 |year=2007 |month=April |pmid=17286835 |doi=10.1111/j.1574-6976.2006.00062.x}}</ref><ref>{{cite journal |author=Newton GL, Fahey RC |title=Mycothiol biochemistry |journal=Arch. Microbiol. |volume=178 |issue=6 |pages=388–94 |year=2002 |month=December |pmid=12420157 |doi=10.1007/s00203-002-0469-4}}</ref> |
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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|s2cid=23893254 }}</ref> |
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==See also== |
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== See also == |
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* ], analogous function in other Bacteria |
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* ], analogous function in other Bacteria |
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* ] |
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==References== |
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== References == |
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Mycobacterium tuberculosis is extraordinarily sensitive to killing by a vitamin C-induced Fenton reaction |
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Published 21 May 2013. Nature Communications4, |
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Article number:1881 doi:10.1038/ncomms2898 |
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==External links== |
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