Mycothiol

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Structural formula
Structural formula of mycothiol
General
Surname Mycothiol
Molecular formula C 17 H 30 N 2 O 12 S
Brief description

White dust

External identifiers / databases
CAS number 192126-76-4
PubChem 441148
ChemSpider 389940
Wikidata Q4382082
properties
Molar mass 486.50 g mol −1
Physical state

firmly

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Mycothiol (MSH or AcCys-GlcN-Ins) is a bacterial thiol that occurs in actinobacteria and acts analogously to glutathione in eukaryotes. Mycothiol is used by the bacteria to break down reactive oxygen species and to detoxify them , including some antibiotics .

It consists of a cysteine component with an acetylated amino group attached to glucosamine . Again, this is linked to inositol . The oxidized disulfide form of mycothiol (MSSM) is called mycothion, which is reduced to mycothiol by the flavoprotein mycothion reductase.

Mycothiol biosynthesis enzymes and mycothiol-dependent enzymes such as mycothiol-dependent formaldehyde dehydrogenase and mycothion reductase are being taken as target substances for the development of treatments for tuberculosis .

Web links

Individual evidence

  1. ↑ K. Ajayi, S. Knapp, RC Lapo, VV Thakur: Intramolecular α-Glucosaminidation: Synthesis of Mycothiol. In: Org. Letters . Volume 12, 2010, pp. 2630-2633, doi: 10.1021 / ol1008334 .
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ F. supporter, MW Vetting, PA Frantom, JS Blanchard: Structures and mechanisms of the biosynthetic enzymes Mycothiol. In: Current opinion in chemical biology. Volume 13, Number 4, October 2009, pp. 451-459, doi: 10.1016 / j.cbpa.2009.07.018 . PMID 19699138 . PMC 2749902 (free full text).
  4. ↑ RC Fahey: Novel thiols of prokaryotes . In: Annu. Rev. Microbiol. tape 55 , 2001, p. 333-356 , doi : 10.1146 / annurev.micro.55.1.333 , PMID 11544359 .
  5. ↑ VK Jothivasan, CJ Hamilton: Mycothiol: synthesis, biosynthesis and biological functions of the major low molecular weight thiol in actinomycetes. In: Natural Product Reports . Volume 25, 2008, pp. 1091-1117, doi: 10.1039 / B616489G
  6. ^ RC Fahey: Glutathione analogs in prokaryotes. In: Biochimica et Biophysica Acta . Volume 1830, number 5, May 2013, pp. 3182-3198, doi: 10.1016 / j.bbagen.2012.10.006 . PMID 23075826 .
  7. ^ GL Newton, N. Buchmeier, RC Fahey: Biosynthesis and functions of mycothiol, the unique protective thiol of Actinobacteria. In: Microbiology and molecular biology reviews: MMBR. Volume 72, Number 3, September 2008, pp. 471-494, doi: 10.1128 / MMBR.00008-08 . PMID 18772286 . PMC 2546866 (free full text).
  8. ^ GL Newton, N. Buchmeier, RC Fahey: Biosynthesis and functions of mycothiol, the unique protective thiol of Actinobacteria . In: Microbiol. Mol. Biol. Rev. Band 72 , no. 3 , September 2008, p. 471-494 , doi : 10.1128 / MMBR.00008-08 , PMID 18772286 , PMC 2546866 (free full text).
  9. ↑ MP Patel, JS Blanchard: Expression, purification, and characterization of Mycobacterium tuberculosis mycothione reductase . In: Biochemistry . tape 38 , no. 36 , September 1999, p. 11827-11833 , doi : 10.1021 / bi991025h , PMID 10512639 .
  10. ^ MP Patel, JS Blanchard: Mycobacterium tuberculosis mycothione reductase: pH dependence of the kinetic parameters and kinetic isotope effects . In: Biochemistry . tape 40 , no. 17 , May 2001, p. 5119-5126 , doi : 10.1021 / bi0029144 , PMID 11318633 .
  11. ↑ M. Rawat, Y. Av-Gay: Mycothiol-dependent proteins in actinomycetes . In: FEMS Microbiol. Rev. Band 31 , no. 3 , April 2007, p. 278-292 , doi : 10.1111 / j.1574-6976.2006.00062.x , PMID 17286835 .
  12. ^ GL Newton, RC Fahey: Mycothiol biochemistry . In: Arch. Microbiol. tape 178 , no. 6 , December 2002, p. 388-394 , doi : 10.1007 / s00203-002-0469-4 , PMID 12420157 .