Surf Wiki
Save to docs
general/coenzymes

From Surf Wiki (app.surf) — the open knowledge base

Coenzyme M

| NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = Coenzyme M is a coenzyme required for methyl-transfer reactions in the metabolism of archaeal methanogens, and in the metabolism of other substrates in bacteria. 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. 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. The coenzyme is an anion with the formula . 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

Methanogenesis

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

: CH3–S–CoM + HS–CoB → CH4 + CoB–S–S–CoM

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

CH3-S-CoM is produced by the MtaA-catalyzed reaction between a methylated version of monomethylamine corrinoid protein MtmC and HS-CoM. The methylated version of MtmC is in turn produced by a cobamide-dependent methyltransferase that uses trimethylamine (TMA), dimethylamine (DMA), or monomethylamine (MMA) as the methyl donor.

Alkene metabolism

Coenzyme M is also used to make acetoacetate from CO2 and propylene or ethylene in aerobic bacteria. Specifically, in bacteria that oxidize alkenes into epoxides. After the propylene (or other alkene) undergoes epoxidation and becomes epoxypropane it becomes electrophilic and toxic. These epoxides react with DNA and proteins, affecting cell function. Alkene-oxidizing bacteria like Xanthobacter autotrophicus use a metabolic pathway in which CoM is conjugated with an aliphatic epoxide. This step creates a nucleophilic compound which can react with CO2. The eventual carboxylation produces acetoacetate, breaking down the propylene.

Biosynthesis

Bacteria and archaea use different synthetic routes, albeit both starting with phosphoenolpyruvate.

References

References

  1. (1979). "Specificity and biological distribution of coenzyme M (2-mercaptoethanesulfonic acid)". J. Bacteriol..
  2. (10 August 1974). "Structure and methylation of coenzyme M({{chem". J. Biol. Chem..
  3. (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.
  4. (September 2008). "Getting a Handle on the Role of Coenzyme M in Alkene Metabolism". Microbiology and Molecular Biology Reviews.
  5. Parry, Ronald J.. (1999-01-01). "1.29 - Biosynthesis of Sulfur-containing Natural Products". Pergamon.
  6. Thauer, Rudolf K.. (1998-09-01). "Biochemistry of methanogenesis: a tribute to Marjory Stephenson:1998 Marjory Stephenson Prize Lecture". Microbiology.
  7. (January 2009). "RamA, a Protein Required for Reductive Activation of Corrinoid-dependent Methylamine Methyltransferase Reactions in Methanogenic Archaea". Journal of Biological Chemistry.
  8. (6 September 2022). "The pathway for coenzyme M biosynthesis in bacteria". Proceedings of the National Academy of Sciences.
Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

coenzymes thiols sulfonates
Want to explore this topic further?

Ask Mako anything about Coenzyme M — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report