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
CAS Number	3375-50-6 sulfonic acid form 40292-31-7 sulfonate form
3D model (Jmol)	Interactive image
ChEBI	CHEBI:58319 Y
ChemSpider	3935 Y
PubChem	4077
InChI InChI=1S/C2H6O3S2/c3-7(4,5)2-1-6/h6H,1-2H2,(H,3,4,5)/p-1 Y Key: ZNEWHQLOPFWXOF-UHFFFAOYSA-M Y
SMILES [O-]S(=O)(=O)CCS
Properties
Chemical formula	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).
Infobox references

Coenzyme M is a coenzyme required for methyl-transfer reactions in the metabolism of methanogens. 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.

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

This induction is catalyzed by the enzyme methyl-coenzyme M reductase, which restricts cofactor F430 as the prosthetic group.