Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
twitter

MetaCyc Compound: dimethylsulfoniopropanoate

Abbrev Name: DMSP

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

Summary:
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

SMILES: C[S+](C)CCC(=O)[O-]

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

InChIKey: InChIKey=DFPOZTRSOAQFIK-UHFFFAOYSA-N

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

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

Reactions known to consume the compound:

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

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

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

Reactions known to produce the compound:

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

dimethylsulfoniopropionate biosynthesis III (algae) :
dimethylsulfonio-2-hydroxybutanoate + H2O → dimethylsulfoniopropanoate + CO2 + 4 H+

In Reactions of unknown directionality:

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


References

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 18.5 on Fri Nov 21, 2014, BIOCYC13B.