Coenzyme M

Coenzyme M
Names
IUPAC name
2-Sulfanylethanesulfonate
Systematic IUPAC name
2-Sulfanylethanesulfonate
Other names
2-mercaptoethylsulfonate; 2-mercaptoethanesulfonate; coenzyme M anion; H-S-CoM; AC1L1HCY; 2-sulfanylethane-1-sulfonate; CTK8A8912
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)/p-1 checkY
    Key: ZNEWHQLOPFWXOF-UHFFFAOYSA-M checkY
  • [O-]S(=O)(=O)CCS
Properties
C2H5O3S2
Molar mass 141.18 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coenzyme M is a coenzyme required for methyl-transfer reactions in the metabolism of archaeal methanogens,[1][2] and in the metabolism of other substrates in bacteria.[3] It is also a necessary cofactor in the metabolic pathway of alkene-oxidizing bacteria. CoM helps eliminate the toxic epoxides formed from the oxidation of alkenes such as propylene.[4] The structure of this coenzyme was discovered by CD Taylor and RS Wolfe in 1974 while they were studying methanogenesis, the process by which carbon dioxide is transformed into methane in some archaea.[5] The coenzyme is an anion with the formula HSCH
2CH
2SO−
3. It is named 2-mercaptoethanesulfonate and abbreviated HS–CoM. The cation is unimportant, but the sodium salt is most available. Mercaptoethanesulfonate contains both a thiol, which is the main site of reactivity, and a sulfonate group, which confers solubility in aqueous media.

  1. ^ Balch WE, Wolfe RS (1979). "Specificity and biological distribution of coenzyme M (2-mercaptoethanesulfonic acid)". J. Bacteriol. 137 (1): 256–63. doi:10.1128/JB.137.1.256-263.1979. PMC 218444. PMID 104960.
  2. ^ Taylor CD, Wolfe RS (10 August 1974). "Structure and methylation of coenzyme M(HSCH
    2    CH
    2    SO
    3    )"    . J. Biol. Chem. 249 (15): 4879–85. doi:10.1016/S0021-9258(19)42403-4. PMID 4367810.
  3. ^ Partovi, Sarah E.; Mus, Florence; Gutknecht, Andrew E.; Martinez, Hunter A.; Tripet, Brian P.; Lange, Bernd Markus; DuBois, Jennifer L.; Peters, John W. (2018-04-06). "Coenzyme M biosynthesis in bacteria involves phosphate elimination by a functionally distinct member of the aspartase/fumarase superfamily". The Journal of Biological Chemistry. 293 (14): 5236–5246. doi:10.1074/jbc.RA117.001234. ISSN 1083-351X. PMC 5892593. PMID 29414784.
  4. ^ Krishnakumar, Arathi M.; Sliwa, Darius; Endrizzi, James A.; Boyd, Eric S.; Ensign, Scott A.; Peters, John W. (September 2008). "Getting a Handle on the Role of Coenzyme M in Alkene Metabolism". Microbiology and Molecular Biology Reviews. 72 (3): 445–456. doi:10.1128/MMBR.00005-08. ISSN 1092-2172. PMC 2546864. PMID 18772284.
  5. ^ Parry, Ronald J. (1999-01-01), Barton, Sir Derek; Nakanishi, Koji; Meth-Cohn, Otto (eds.), "1.29 - Biosynthesis of Sulfur-containing Natural Products", Comprehensive Natural Products Chemistry, Oxford: Pergamon, pp. 825–863, doi:10.1016/b978-0-08-091283-7.00031-x, ISBN 978-0-08-091283-7, retrieved 2022-05-10