Coenzyme M
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| Names | |
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| IUPAC name
2-Sulfanylethanesulfonate
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| Systematic IUPAC name
2-Sulfanylethanesulfonate
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| Other names
2-mercaptoethylsulfonate; 2-mercaptoethanesulfonate; coenzyme M anion; H-S-CoM; AC1L1HCY; 2-sulfanylethane-1-sulfonate; CTK8A8912
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| Identifiers | |
| ChEBI | CHEBI:58319  |
| ChemSpider | 3935 |
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| Jmol interactive 3D | Image |
| PubChem | 4077 |
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| Properties | |
| C2H5O3S2 | |
| Molar mass | 141.18 g·mol−1 |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Coenzyme M is a coenzyme required for methyl-transfer reactions in the metabolism of methanogens.[1][2] 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.
Biochemical role[edit]
The coenzyme is the C1 donor in methanogenesis. It is converted to propyl coenzyme M-thioester, the thioether CH
3SCH
2CH
2SO−
3, in the penultimate step to methane formation.[3] Coenzyme M reacts with coenzyme B, 7-thioheptanoylthreoninephosphate, to give a homodisulfide, releasing methane:
- CH
3–S–CoM + HS–CoB → CH
4 + CoB–S–S–CoM
This induction is catalyzed by the enzyme methyl-coenzyme M reductase, which restricts cofactor F430 as the prosthetic group.
See also[edit]
- Mesna – a cancer chemotherapy adjuvant with the same parent structure
References[edit]
- ^ Balch WE, Wolfe RS (1979). "Specificity and biological distribution of coenzyme M (2-mercaptoethanesulfonic acid)". J. Bacteriol. 137 (1): 256–63. PMC 218444. PMID 104960.
- ^ Taylor CD, Wolfe RS (10 August 1974). "Structure and methylation of coenzyme M(HSCH
2CH
2SO
3)". J. Biol. Chem. 249 (15): 4879–85. PMID 4367810. - ^ Thauer RK (1998). "Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson". Microbiology 144 (9): 2377–2406. doi:10.1099/00221287-144-9-2377. PMID 9782487.
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