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词条 Coenzyme M
释义

  1. Biochemical role

  2. See also

  3. References

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| Name = Coenzyme M
| ImageFile = Coenzyme M (CoM).svg
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| IUPACName = 2-Sulfanylethanesulfonate
| SystematicName = 2-Sulfanylethanesulfonate
| OtherNames = 2-mercaptoethylsulfonate; 2-mercaptoethanesulfonate; coenzyme M anion; H-S-CoM; AC1L1HCY; 2-sulfanylethane-1-sulfonate; CTK8A8912
|Section1={{Chembox Identifiers
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| CASNo1 = 3375-50-6
| CASNo1_Comment = sulfonic acid form
| CASNo2 = 40292-31-7
| CASNo2_Comment = sulfonate form
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| PubChem = 4077
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| SMILES = [O-]S(=O)(=O)CCS
| InChI =
| StdInChI = 1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)/p-1
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| StdInChIKey = ZNEWHQLOPFWXOF-UHFFFAOYSA-M
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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 {{chem|HSCH|2|CH|2|SO|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

The coenzyme is the C1 donor in methanogenesis. It is converted to methyl-coenzyme M thioether, the thioether {{chem|CH|3|SCH|2|CH|2|SO|3|-}}, in the penultimate step to methane formation.[3] Methyl-coenzyme M reacts with coenzyme B, 7-thioheptanoylthreoninephosphate, to give a heterodisulfide, releasing methane:

{{chem|CH|3|–S–CoM}} + HS–CoB → {{chem|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

  • Mesna – a cancer chemotherapy adjuvant with the same structure

References

1. ^{{cite journal |vauthors=Balch WE, Wolfe RS |title=Specificity and biological distribution of coenzyme M (2-mercaptoethanesulfonic acid) |journal=J. Bacteriol. |volume=137 |issue=1 |pages=256–63 |year=1979 |pmid=104960 |pmc=218444}}
2. ^{{cite journal |vauthors=Taylor CD, Wolfe RS |title=Structure and methylation of coenzyme M({{chem|HSCH|2|CH|2|SO|3}}) |journal=J. Biol. Chem. |volume=249 |issue=15 |pages=4879–85 |date=10 August 1974|pmid=4367810 |url=http://www.jbc.org/cgi/reprint/249/15/4879 }}
3. ^{{cite journal | doi=10.1099/00221287-144-9-2377 | author=Thauer RK | title=Biochemistry of Methanogenesis: a Tribute to Marjory Stephenson | journal = Microbiology | year = 1998 | volume = 144 | issue = 9| pages=2377–2406 | pmid=9782487 |url=http://mic.sgmjournals.org/cgi/pmidlookup?view=long&pmid=9782487 }}
{{Enzyme cofactors}}{{biochem-stub}}

3 : Coenzymes|Thiols|Sulfonates

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