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{{Short description|Chemical compound}} |
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|ImageFile=Dimethylsulfoniopropionate-2D-skeletal.png |
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| verifiedrevid = 442151753 |
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|ImageSize=150px |
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| ImageFile =Dimethylsulfoniopropionate Structural Formula V1.svg |
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|IUPACName=(Dimethylsulfaniumyl)propanoate |
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| ImageSize =170px |
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|OtherNames=dimethyl-β-propiothetin |
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| ImageAlt = Skeletal formula of dimethylsulfoniopropionate |
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|Section1= {{Chembox Identifiers |
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| ImageFile1 = Dimethylsulfoniopropionate zwitterion 3D ball.png |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ImageSize1 = 170 |
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| ChemSpiderID = 11207615 |
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| ImageAlt1 = Ball-and-stick model of the dimethylsulfoniopropionate zwitterion |
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| InChI = 1/C5H10O2S/c1-4(5(6)7)8(2)3/h4H,1-3H3 |
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| IUPACName = 3-dimethylsulfoniopropanoate |
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| InChIKey = SAFXJAMOKWMNRO-UHFFFAOYAC |
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| OtherNames =dimethyl-β-propiothetin<br/>''S'',''S''-dimethyl-β-propiothetin |
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| SMILES1 = C(C)C(C)C()=O |
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|Section1={{Chembox Identifiers |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| StdInChI = 1S/C5H10O2S/c1-4(5(6)7)8(2)3/h4H,1-3H3 |
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| ChemSpiderID = 22195 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| InChI = 1/C5H10O2S/c1-8(2)4-3-5(6)7/h3-4H2,1-2H3 |
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| StdInChIKey = SAFXJAMOKWMNRO-UHFFFAOYSA-N |
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| InChIKey = DFPOZTRSOAQFIK-UHFFFAOYAW |
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| CASNo=7314-30-9 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| PubChem=23736 |
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| StdInChI = 1S/C5H10O2S/c1-8(2)4-3-5(6)7/h3-4H2,1-2H3 |
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| SMILES=C(C)CCC(=O) |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = DFPOZTRSOAQFIK-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo =7314-30-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = C884XA7QGG |
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| PubChem =23736 |
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| SMILES =C(C)CCC(=O) |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>5</sub>H<sub>10</sub>O<sub>2</sub>S |
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| Formula =C<sub>5</sub>H<sub>10</sub>O<sub>2</sub>S |
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| MolarMass=134.1967 |
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| MolarMass =134.1967 |
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| Appearance =white crystalline hygroscopic powder with a characteristic odor.<ref>{{cite web |url=http://tianyuchem.en.alibaba.com/product/538880245-213360543/FACTORYSALE_Dimethylpropiothetin_7314_30_9.html |title=Http 404 |access-date=2013-02-05 |url-status=dead |archive-url=https://archive.today/20130306163118/http://tianyuchem.en.alibaba.com/product/538880245-213360543/FACTORYSALE_Dimethylpropiothetin_7314_30_9.html |archive-date=2013-03-06 }}</ref> |
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| MeltingPtC = 120 to 125 |
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| MeltingPt_ref = <ref>{{cite web |url=http://tianyuchem.en.alibaba.com/product/538880245-213360543/FACTORYSALE_Dimethylpropiothetin_7314_30_9.html |title=Http 404 |access-date=2013-02-05 |url-status=dead |archive-url=https://archive.today/20130306163118/http://tianyuchem.en.alibaba.com/product/538880245-213360543/FACTORYSALE_Dimethylpropiothetin_7314_30_9.html |archive-date=2013-03-06 }}</ref> |
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|Section3= {{Chembox Hazards |
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'''Dimethylsulfoniopropionate''' (frequently abbreviated to DMSP), is an ] with the chemical formula|formula]] (CH<sub>3</sub>)<sub>2</sub>S<sup>+</sup>CH<sub>2</sub>CH<sub>2</sub>COO<sup>−</sup>. This ] ] found in marine ], ], and some species of terrestrial and aquatic ]. It functions as an ] as well as several other physiological and environmental roles have also been identified.<ref>{{Cite journal |
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'''Dimethylsulfoniopropionate''' ('''DMSP'''), is an ] with the ] (CH<sub>3</sub>)<sub>2</sub>S<sup>+</sup>CH<sub>2</sub>CH<sub>2</sub>COO<sup>−</sup>. This ]ic ] can be found in marine ], ], and some species of terrestrial and aquatic ]. It functions as an ] as well as several other physiological and environmental roles have also been identified.<ref>{{Cite journal|last=DeBose|first=Jennifer L.|author2=Sean C. Lema|author3=Gabrielle A. Nevitt|date=2008-03-07|title=Dimethylsulfoniopropionate as a foraging cue for reef fishes|journal=Science|volume=319|issue=5868|pages=1356|doi=10.1126/science.1151109|pmid=18323445|bibcode=2008Sci...319.1356D|s2cid=20782786|url=https://digitalcommons.calpoly.edu/cgi/viewcontent.cgi?article=1339&context=bio_fac}}{{Cite journal|last=Vila-Costa|first=Maria|author2=Rafel Simo|author3=Hyakubun Harada|author4=Josep M. Gasol|author5=Doris Slezak|author6=Ronald P. Kiene|date=2006-10-27|title=Dimethylsulfoniopropionate uptake by marine phytoplankton|journal=Science|volume=314|issue=5799|pages=652–654|doi=10.1126/science.1131043|pmid=17068265|bibcode=2006Sci...314..652V|s2cid=27541024}}</ref> DMSP was first identified in the marine red alga '']''.<ref>{{Cite journal| doi = 10.1039/JR9480001591| volume = 3| pages = 1591–1597| last = Challenger| first = Frederick| author2 = Margaret Isabel Simpson| title = Studies on biological methylation. Part XII. A precursor of the dimethyl sulphide evolved by Polysiphonia fastigiata. Dimethyl-2-carboxyethylsulphonium hydroxide and its salts| journal = Journal of the Chemical Society | year=1948|pmid = 18101461}}</ref> |
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| doi = 10.1126/science.1151109 |
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| volume = 319 |
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| issue = 5868 |
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| pages = 1356 |
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| last = DeBose |
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| first = Jennifer L. |
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| coauthors = Sean C. Lema, Gabrielle A. Nevitt |
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| title = Dimethylsulfoniopropionate as a foraging cue for reef fishes |
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| journal = Science |
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| accessdate = 2008-03-21 |
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| date = 2008-03-07 |
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| url = http://www.sciencemag.org/cgi/content/abstract/319/5868/1356 |
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| format = abstract |
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| pmid = 18323445 |
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}}{{Cite journal |
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| doi = 10.1126/science.1131043 |
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| volume = 314 |
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| issue = 5799 |
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| pages = 652–654 |
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| last = Vila-Costa |
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| first = Maria |
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| coauthors = Rafel Simo, Hyakubun Harada, Josep M. Gasol, Doris Slezak, Ronald P. Kiene |
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| ⚫ |
| title = Dimethylsulfoniopropionate uptake by marine phytoplankton |
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| journal = Science |
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| accessdate = 2008-03-21 |
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| date = 2006-10-27 |
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| url = http://www.sciencemag.org/cgi/content/abstract/314/5799/652 |
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| format = abstract |
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| pmid = 17068265 |
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}}</ref> |
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==Biosynthesis== |
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==Biosynthesis== |
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In higher plants, DMSP is biosynthesized from S-methylmethionine. Two intermediates in this conversion are dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.<ref>Scott D. McNeil, Michael L. Nuccio, and Andrew D. Hanson "Betaines and Related Osmoprotectants. Targets for Metabolic Engineering of Stress Resistance" Plant Physiology, August 1999, Vol. 120, pp. 945–949. {{DOI|10.1104/pp.120.4.945}}</ref> In algae, however, the biosynthesis starts with removal of the amino group from methionine, rather than from S-methylmethionine. |
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In higher plants, DMSP is biosynthesized from ]. Two intermediates in this conversion are dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.<ref>{{cite journal | last1 = McNeil | first1 = Scott D. | last2 = Nuccio | first2 = Michael L. | last3 = Hanson | first3 = Andrew D. | year = 1999 | title = Betaines and Related Osmoprotectants. Targets for Metabolic Engineering of Stress Resistance | journal = Plant Physiology | volume = 120 | issue = 4| pages = 945–949 | doi = 10.1104/pp.120.4.945| pmid = 10444077 | pmc = 1539222 }}</ref> In algae, however, the biosynthesis starts with the replacement of the amino group in ] by hydroxide.<ref>{{cite journal |doi=10.1038/nmicrobiol.2017.9|title=Dimethylsulfoniopropionate Biosynthesis in Marine Bacteria and Identification of the Key Gene in this Process|year=2017|last1=Curson|first1=Andrew R. J.|last2=Liu|first2=Ji|last3=Bermejo Martínez|first3=Ana|last4=Green|first4=Robert T.|last5=Chan|first5=Yohan|last6=Carrión|first6=Ornella|last7=Williams|first7=Beth T.|last8=Zhang|first8=Sheng-Hui|last9=Yang|first9=Gui-Peng|last10=Bulman Page|first10=Philip C.|last11=Zhang|first11=Xiao-Hua|last12=Todd|first12=Jonathan D.|journal=Nature Microbiology|volume=2|issue=5|page=17009|pmid=28191900|s2cid=21460292|url=https://ueaeprints.uea.ac.uk/id/eprint/62649/1/Todd_Figure_1.pdf }}</ref> |
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==Degradation== |
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==Degradation== |
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DMSP is broken down by marine microbes to form two major volatile sulfur products, each with distinct effects on the environment. Its major breakdown product is ] (CH<sub>3</sub>SH), which is assimilated by bacteria into ] sulfur. Its second volatile breakdown product is ] (CH<sub>3</sub>SCH<sub>3</sub>; DMS). Most DMS in seawater is cleaved from DMSP by the enzyme DMSP ], although many non-marine species of bacteria convert ] to DMS.{{Citation needed|date=April 2011}} |
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DMSP is broken down by marine microbes to form two major volatile sulfur products, each with distinct effects on the environment. One of its breakdown products is ] (CH<sub>3</sub>SH), which is assimilated by bacteria into ] sulfur. Another volatile breakdown product is ] (CH<sub>3</sub>SCH<sub>3</sub>; DMS). There is evidence that DMS in seawater can be produced by cleavage of dissolved (extracellular) DMSP<ref>{{Cite journal|year=1993|title=Characterization of a DMSP-degrading bacterial isolate from the Sargasso Sea|journal=Archives of Microbiology|volume=160|issue=4|pages=312–318|doi=10.1007/bf00292083|last1=Ledyard|first1=Kathleen M.|last2=Delong|first2=Edward F.|last3=Dacey|first3=John W. H.|s2cid=33566366}}</ref><ref>{{Cite journal|year=2002|title=Dimethylsulfoniopropionate: Its sources, role in the marine food web, and biological degradation to dimethylsulfide|journal=Applied and Environmental Microbiology|volume=68|issue=12|pages=5804–15|doi=10.1128/aem.68.12.5804-5815.2002|pmid=12450799|last1=Yoch|first1=D. C.|doi-access=free|pmc=134419|bibcode=2002ApEnM..68.5804Y}}</ref> by the enzyme ], although many non-marine species of bacteria convert methanethiol to DMS.{{Citation needed|date=April 2011}} |
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DMS is also taken up by marine ], but not as rapidly as methanethiol. Although DMS usually consists of less than 25% of the volatile breakdown products of DMSP, the high reactivity of methanethiol makes the steady-state DMS concentrations in seawater approximately 10 times those of methanethiol (~3 ] vs. ~0.3 nM). Curiously, there have never been any published correlations between the concentrations of DMS and methanethiol. This is probably due to the non-linear ] and microbial uptake of methanethiol in seawater, and the comparatively low reactivity of DMS. However, a significant portion of ] in seawater is ] to ] (DMSO). |
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DMS is also taken up by ], but not as rapidly as methanethiol. Although DMS usually consists of less than 25% of the volatile breakdown products of DMSP, the high reactivity of methanethiol makes the steady-state DMS concentrations in seawater approximately 10 times those of methanethiol (~3 ] vs. ~0.3 nM). Curiously, there have never been any published correlations between the concentrations of DMS and methanethiol. This is probably due to the non-linear ] and microbial uptake of methanethiol in seawater, and the comparatively low reactivity of DMS. However, a significant portion of DMS in seawater is ] to ] (DMSO). |
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Relevant to ], DMS is thought to play a role in the Earth's heat budget by decreasing the amount of ] that reaches the Earth's surface. |
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Relevant to ], DMS is thought to play a role in the Earth's heat budget by decreasing the amount of ] that reaches the Earth's surface. This occurs through degradation of DMS in the atmosphere into hygroscopic compounds that condense water vapor leading to the formation of clouds.<ref>{{Cite web | url=http://www.whoi.edu/oceanus/feature/dms--the-climate-gas-youve-never-heard-of | title=DMS: The Climate Gas You've Never Heard of}}</ref> |
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DMSP has also been implicated in influencing the taste and odour characteristics of various products. For example, although DMSP is odourless and tasteless, it is accumulated at high levels in some marine ] or ]s. Increased growth rates, vigour and stress resistance among animals cultivated on such diets have been reported.{{Citation needed|date=April 2011}} DMS, is responsible for repellent, 'off' tastes and odours that develop in some seafood products because of the action of bacterial DMSP-], which cogenerates ]. |
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DMSP has also been implicated in influencing the taste and odour characteristics of various products. For example, although DMSP is odourless and tasteless, it is accumulated at high levels in some marine ] or ]s. Increased growth rates, vigour and stress resistance among animals cultivated on such diets have been reported.{{Citation needed|date=April 2011}}<ref>{{Citation|last=Nakajima|first=Kenji|chapter=Effects of DMSP and Related Compounds on Behavior, Growth and Stress Resistance of Fish, Amphibians and Crustaceans|date=1996|pages=165–176|editor-last=Kiene|editor-first=R. P.|publisher=Springer, Boston, MA|language=en|doi=10.1007/978-1-4613-0377-0_15|isbn=9780306453069|editor2-last=Visscher|editor2-first=P. T.|editor3-last=Keller|editor3-first=M. D.|editor4-last=Kirst|editor4-first=G. O.|title=Biological and Environmental Chemistry of DMSP and Related Sulfonium Compounds}}</ref> DMS, is responsible for repellent, 'off' tastes and odours that develop in some ] because of the action of bacterial DMSP-lyase, which cogenerates ]. |
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==Further reading== |
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*{{cite book|author=Kenji Nakajima|chapter=Amelioration Effect of a Tertiary Sulfonium Compound, Dimethylsulfoniopropionate|pages=205–238|editor=S.-K. Kim|title=Handbook of Anticancer Drugs from Marine Origin|publisher=Springer|doi=10.1007/978-3-319-07145-9_11|year=2015|isbn=978-3-319-07144-2}} |
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==See also== |
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==See also== |
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* ], proposing a feedback loop that operates between ocean ecosystems and the Earth's climate |
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* ], proposing a feedback loop that operates between ocean ecosystems and the Earth's climate |
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* ], a group of marine unicellular planktonic photosynthetic algae, producer of DMSP |
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* ], a group of marine unicellular planktonic photosynthetic algae, producer of DMSP |
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* ], a breakdown product of DMSP along with ] |
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* ], a breakdown product of DMSP along with ] |
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* Dimethyl selenide, a selenium analogue of DMS produced by bacteria and phytoplankton |
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* ], a selenium analogue of DMS produced by bacteria and phytoplankton |
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* ], a coccolithophorid producing DMSP |
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* '']'', a coccolithophorid producing DMSP |
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==References== |
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==References== |
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==External links== |
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