Coenzyme M

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| Name = Coenzyme M

| ImageFile = Coenzyme M (CoM).svg

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| ImageFile2 = Coenzyme M 3D BS.png

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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)

| PubChem = 4077

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| ChemSpiderID = 3935

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| UNII1 = VHD28S0H7F

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| UNII1_Comment = (sulfonic acid form)

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| ChEBI = 58319

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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

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ZNEWHQLOPFWXOF-UHFFFAOYSA-M

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|Section2={{Chembox Properties

| C=2 | H=5 | O=3 | S=2

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|Section3={{Chembox Structure

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|Section4={{Chembox Thermochemistry

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|Section5={{Chembox Pharmacology

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|Section8={{Chembox Related

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Coenzyme M is a coenzyme required for methyl-transfer reactions in the metabolism of archaeal methanogens,{{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 |doi=10.1128/JB.137.1.256-263.1979}}{{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 |doi=10.1016/S0021-9258(19)42403-4 |pmid=4367810 |doi-access=free }} and in the metabolism of other substrates in bacteria.{{Cite journal|last1=Partovi|first1=Sarah E.|last2=Mus|first2=Florence|last3=Gutknecht|first3=Andrew E.|last4=Martinez|first4=Hunter A.|last5=Tripet|first5=Brian P.|last6=Lange|first6=Bernd Markus|last7=DuBois|first7=Jennifer L.|last8=Peters|first8=John W.|date=2018-04-06|title=Coenzyme M biosynthesis in bacteria involves phosphate elimination by a functionally distinct member of the aspartase/fumarase superfamily|journal=The Journal of Biological Chemistry|volume=293|issue=14|pages=5236–5246|doi=10.1074/jbc.RA117.001234|issn=1083-351X|pmc=5892593|pmid=29414784|doi-access=free }} 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.{{Cite journal |last1=Krishnakumar |first1=Arathi M. |last2=Sliwa |first2=Darius |last3=Endrizzi |first3=James A. |last4=Boyd |first4=Eric S. |last5=Ensign |first5=Scott A. |last6=Peters |first6=John W. |date=September 2008 |title=Getting a Handle on the Role of Coenzyme M in Alkene Metabolism |journal=Microbiology and Molecular Biology Reviews |volume=72 |issue=3 |pages=445–456 |doi=10.1128/MMBR.00005-08 |issn=1092-2172 |pmc=2546864 |pmid=18772284}} 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.{{Citation |last=Parry |first=Ronald J. |title=1.29 - Biosynthesis of Sulfur-containing Natural Products |date=1999-01-01 |url=https://www.sciencedirect.com/science/article/pii/B978008091283700031X |work=Comprehensive Natural Products Chemistry |pages=825–863 |editor-last=Barton |editor-first=Sir Derek |place=Oxford |publisher=Pergamon |language=en |doi=10.1016/b978-0-08-091283-7.00031-x |isbn=978-0-08-091283-7 |access-date=2022-05-10 |editor2-last=Nakanishi |editor2-first=Koji |editor3-last=Meth-Cohn |editor3-first=Otto}} 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.