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MetaCyc Compound: dimethylsulfoniopropanoate

Abbrev Name: DMSP

Synonyms: S,S-dimethyl-β-propiothetin, DMPT, DMSP, dimethylpropiothetin, S-dimethylsulfonium propionic acid, dimethylsulfoniopropionate

Dimethylsulfoniopropanoate (DMSP), an osmolyte of many marine algae and certain plants [Otte04], is also the main source for dimethyl sulfide (DMS) in the marine environment [Yoch02]. Marine phytoplankton synthesize DMSP not only as an osmolyte, but also as a predator deterrent and an antioxidant [Howard06]. The degradation of DMSP to DMS and subsequent exchange of DMS across the ocean-atmosphere boundary is the main natural source of sulfur to the atmosphere.

Chemical Formula: C5H10O2S

Molecular Weight: 134.19 Daltons

Monoisotopic Molecular Weight: 135.0479752873 Daltons

dimethylsulfoniopropanoate compound structure


InChI: InChI=1S/C5H10O2S/c1-8(2)4-3-5(6)7/h3-4H2,1-2H3


Unification Links: CAS:7314-30-9, ChEBI:16457, ChemSpider:22195, KEGG:C04022, MetaboLights:MTBLC16457, PubChem:23736

Standard Gibbs Free Energy of Formation (ΔfG in kcal/mol): 37.4512Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

dimethylsulfoniopropanoate degradation I (cleavage) , superpathway of dimethylsulfoniopropanoate degradation :
dimethylsulfoniopropanoate → dimethyl sulfide + acrylate + H+

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation III (demethylation) :
3-(methylthio)propanoate + an N5-methyl-tetrahydrofolate + H+dimethylsulfoniopropanoate + a tetrahydrofolate

Reactions known to produce the compound:

dimethylsulfoniopropanoate biosynthesis I (Wollastonia) , dimethylsulfoniopropanoate biosynthesis II (Spartina) :
3-dimethylsulfoniopropionaldehyde + NAD+ + H2O → dimethylsulfoniopropanoate + NADH + 2 H+

dimethylsulfoniopropanoate biosynthesis III (algae) :
dimethylsulfonio-2-hydroxybutanoate + 2 an oxidized unknown electron acceptor + H2O → dimethylsulfoniopropanoate + CO2 + 2 an reduced unknown electron acceptor

In Reactions of unknown directionality:

Not in pathways:
dimethylsulfoniopropanoate + H2O = dimethyl sulfide + 3-hydroxypropanoate + H+

This compound has been characterized as an alternative substrate of the following enzymes: L-proline:H+ symporter


Howard06: Howard EC, Henriksen JR, Buchan A, Reisch CR, Burgmann H, Welsh R, Ye W, Gonzalez JM, Mace K, Joye SB, Kiene RP, Whitman WB, Moran MA (2006). "Bacterial taxa that limit sulfur flux from the ocean." Science 314(5799);649-52. PMID: 17068264

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Otte04: Otte ML, Wilson G, Morris JT, Moran BM (2004). "Dimethylsulphoniopropionate (DMSP) and related compounds in higher plants." J Exp Bot 55(404);1919-25. PMID: 15181109

Yoch02: Yoch DC (2002). "Dimethylsulfoniopropionate: its sources, role in the marine food web, and biological degradation to dimethylsulfide." Appl Environ Microbiol 68(12);5804-15. PMID: 12450799

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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