Coenzyme M

Coenzyme M

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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
ChEBI	CHEBI:58319 Y
ChemSpider	3935 Y
Jmol 3D model	Interactive image
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
Vapor pressure	{{{value}}}
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.

Biochemical role

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. 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

• Mesna – a cancer chemotherapy adjuvant with the same parent structure