In higher plants, DMSP is biosynthesized from S-methylmethionine. Two intermediates in this conversion are dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde.[5] In algae, however, the biosynthesis starts with the replacement of the amino group in methionine by hydroxide.[6]
Degradationedit
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 methanethiol (CH3SH), which is assimilated by bacteria into protein sulfur. Another volatile breakdown product is dimethyl sulfide (CH3SCH3; DMS). There is evidence that DMS in seawater can be produced by cleavage of dissolved (extracellular) DMSP[7][8] by the enzyme DMSP-lyase, although many non-marine species of bacteria convert methanethiol to DMS.[citation needed]
DMS is also taken up by marine bacteria, 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 nM 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 abiotic and microbial uptake of methanethiol in seawater, and the comparatively low reactivity of DMS. However, a significant portion of DMS in seawater is oxidized to dimethyl sulfoxide (DMSO).
Relevant to global climate, DMS is thought to play a role in the Earth's heat budget by decreasing the amount of solar radiation 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.[9]
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 herbivores or filter feeders. Increased growth rates, vigour and stress resistance among animals cultivated on such diets have been reported.[citation needed][10] DMS, is responsible for repellent, 'off' tastes and odours that develop in some seafood products because of the action of bacterial DMSP-lyase, which cogenerates acrylate.
Further readingedit
Kenji Nakajima (2015). "Amelioration Effect of a Tertiary Sulfonium Compound, Dimethylsulfoniopropionate". In S.-K. Kim (ed.). Handbook of Anticancer Drugs from Marine Origin. Springer. pp. 205–238. doi:10.1007/978-3-319-07145-9_11. ISBN978-3-319-07144-2.
See alsoedit
CLAW hypothesis, proposing a feedback loop that operates between ocean ecosystems and the Earth's climate
Coccolithophore, a group of marine unicellular planktonic photosynthetic algae, producer of DMSP
^"Http 404". Archived from the original on 2013-03-06. Retrieved 2013-02-05.
^"Http 404". Archived from the original on 2013-03-06. Retrieved 2013-02-05.
^DeBose, Jennifer L.; Sean C. Lema; Gabrielle A. Nevitt (2008-03-07). "Dimethylsulfoniopropionate as a foraging cue for reef fishes". Science. 319 (5868): 1356. Bibcode:2008Sci...319.1356D. doi:10.1126/science.1151109. PMID 18323445. S2CID 20782786.Vila-Costa, Maria; Rafel Simo; Hyakubun Harada; Josep M. Gasol; Doris Slezak; Ronald P. Kiene (2006-10-27). "Dimethylsulfoniopropionate uptake by marine phytoplankton". Science. 314 (5799): 652–654. Bibcode:2006Sci...314..652V. doi:10.1126/science.1131043. PMID 17068265. S2CID 27541024.
^Challenger, Frederick; Margaret Isabel Simpson (1948). "Studies on biological methylation. Part XII. A precursor of the dimethyl sulphide evolved by Polysiphonia fastigiata. Dimethyl-2-carboxyethylsulphonium hydroxide and its salts". Journal of the Chemical Society. 3: 1591–1597. doi:10.1039/JR9480001591. PMID 18101461.
^McNeil, Scott D.; Nuccio, Michael L.; Hanson, Andrew D. (1999). "Betaines and Related Osmoprotectants. Targets for Metabolic Engineering of Stress Resistance". Plant Physiology. 120 (4): 945–949. doi:10.1104/pp.120.4.945. PMC1539222. PMID 10444077.
^Curson, Andrew R. J.; Liu, Ji; Bermejo Martínez, Ana; Green, Robert T.; Chan, Yohan; Carrión, Ornella; Williams, Beth T.; Zhang, Sheng-Hui; Yang, Gui-Peng; Bulman Page, Philip C.; Zhang, Xiao-Hua; Todd, Jonathan D. (2017). "Dimethylsulfoniopropionate Biosynthesis in Marine Bacteria and Identification of the Key Gene in this Process" (PDF). Nature Microbiology. 2 (5): 17009. doi:10.1038/nmicrobiol.2017.9. PMID 28191900. S2CID 21460292.
^Ledyard, Kathleen M.; Delong, Edward F.; Dacey, John W. H. (1993). "Characterization of a DMSP-degrading bacterial isolate from the Sargasso Sea". Archives of Microbiology. 160 (4): 312–318. doi:10.1007/bf00292083. S2CID 33566366.
^Yoch, D. C. (2002). "Dimethylsulfoniopropionate: Its sources, role in the marine food web, and biological degradation to dimethylsulfide". Applied and Environmental Microbiology. 68 (12): 5804–15. Bibcode:2002ApEnM..68.5804Y. doi:10.1128/aem.68.12.5804-5815.2002. PMC134419. PMID 12450799.
^Nakajima, Kenji (1996), "Effects of DMSP and Related Compounds on Behavior, Growth and Stress Resistance of Fish, Amphibians and Crustaceans", in Kiene, R. P.; Visscher, P. T.; Keller, M. D.; Kirst, G. O. (eds.), Biological and Environmental Chemistry of DMSP and Related Sulfonium Compounds, Springer, Boston, MA, pp. 165–176, doi:10.1007/978-1-4613-0377-0_15, ISBN9780306453069
External linksedit
April 13, 2024
dimethylsulfoniopropionate, dmsp, organosulfur, compound, with, formula, ch2ch2coo, this, zwitterionic, metabolite, found, marine, phytoplankton, seaweeds, some, species, terrestrial, aquatic, vascular, plants, functions, osmolyte, well, several, other, physio. Dimethylsulfoniopropionate DMSP is an organosulfur compound with the formula CH3 2S CH2CH2COO This zwitterionic metabolite can be found in marine phytoplankton seaweeds and some species of terrestrial and aquatic vascular plants It functions as an osmolyte as well as several other physiological and environmental roles have also been identified 3 DMSP was first identified in the marine red alga Polysiphonia fastigiata 4 Dimethylsulfoniopropionate NamesIUPAC name 3 dimethylsulfoniopropanoateOther names dimethyl b propiothetinS S dimethyl b propiothetinIdentifiersCAS Number 7314 30 9 Y3D model JSmol Interactive imageChemSpider 22195 NECHA InfoCard 100 228 826PubChem CID 23736UNII C884XA7QGG YCompTox Dashboard EPA DTXSID0041014InChI InChI 1S C5H10O2S c1 8 2 4 3 5 6 7 h3 4H2 1 2H3 NKey DFPOZTRSOAQFIK UHFFFAOYSA N NInChI 1 C5H10O2S c1 8 2 4 3 5 6 7 h3 4H2 1 2H3Key DFPOZTRSOAQFIK UHFFFAOYAWSMILES C S C CCC O O PropertiesChemical formula C5H10O2SMolar mass 134 1967Appearance white crystalline hygroscopic powder with a characteristic odor 1 Melting point 120 to 125 C 248 to 257 F 393 to 398 K 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Biosynthesis 2 Degradation 3 Further reading 4 See also 5 References 6 External linksBiosynthesis editIn higher plants DMSP is biosynthesized from S methylmethionine Two intermediates in this conversion are dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde 5 In algae however the biosynthesis starts with the replacement of the amino group in methionine by hydroxide 6 Degradation editDMSP 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 methanethiol CH3SH which is assimilated by bacteria into protein sulfur Another volatile breakdown product is dimethyl sulfide CH3SCH3 DMS There is evidence that DMS in seawater can be produced by cleavage of dissolved extracellular DMSP 7 8 by the enzyme DMSP lyase although many non marine species of bacteria convert methanethiol to DMS citation needed DMS is also taken up by marine bacteria 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 nM 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 abiotic and microbial uptake of methanethiol in seawater and the comparatively low reactivity of DMS However a significant portion of DMS in seawater is oxidized to dimethyl sulfoxide DMSO Relevant to global climate DMS is thought to play a role in the Earth s heat budget by decreasing the amount of solar radiation 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 9 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 herbivores or filter feeders Increased growth rates vigour and stress resistance among animals cultivated on such diets have been reported citation needed 10 DMS is responsible for repellent off tastes and odours that develop in some seafood products because of the action of bacterial DMSP lyase which cogenerates acrylate Further reading editKenji Nakajima 2015 Amelioration Effect of a Tertiary Sulfonium Compound Dimethylsulfoniopropionate In S K Kim ed Handbook of Anticancer Drugs from Marine Origin Springer pp 205 238 doi 10 1007 978 3 319 07145 9 11 ISBN 978 3 319 07144 2 See also editCLAW hypothesis proposing a feedback loop that operates between ocean ecosystems and the Earth s climate Coccolithophore a group of marine unicellular planktonic photosynthetic algae producer of DMSP Dimethyl sulfide a breakdown product of DMSP along with methanethiol Dimethyl selenide a selenium analogue of DMS produced by bacteria and phytoplankton Emiliania huxleyi a coccolithophorid producing DMSPReferences edit Http 404 Archived from the original on 2013 03 06 Retrieved 2013 02 05 Http 404 Archived from the original on 2013 03 06 Retrieved 2013 02 05 DeBose Jennifer L Sean C Lema Gabrielle A Nevitt 2008 03 07 Dimethylsulfoniopropionate as a foraging cue for reef fishes Science 319 5868 1356 Bibcode 2008Sci 319 1356D doi 10 1126 science 1151109 PMID 18323445 S2CID 20782786 Vila Costa Maria Rafel Simo Hyakubun Harada Josep M Gasol Doris Slezak Ronald P Kiene 2006 10 27 Dimethylsulfoniopropionate uptake by marine phytoplankton Science 314 5799 652 654 Bibcode 2006Sci 314 652V doi 10 1126 science 1131043 PMID 17068265 S2CID 27541024 Challenger Frederick Margaret Isabel Simpson 1948 Studies on biological methylation Part XII A precursor of the dimethyl sulphide evolved by Polysiphonia fastigiata Dimethyl 2 carboxyethylsulphonium hydroxide and its salts Journal of the Chemical Society 3 1591 1597 doi 10 1039 JR9480001591 PMID 18101461 McNeil Scott D Nuccio Michael L Hanson Andrew D 1999 Betaines and Related Osmoprotectants Targets for Metabolic Engineering of Stress Resistance Plant Physiology 120 4 945 949 doi 10 1104 pp 120 4 945 PMC 1539222 PMID 10444077 Curson Andrew R J Liu Ji Bermejo Martinez Ana Green Robert T Chan Yohan Carrion Ornella Williams Beth T Zhang Sheng Hui Yang Gui Peng Bulman Page Philip C Zhang Xiao Hua Todd Jonathan D 2017 Dimethylsulfoniopropionate Biosynthesis in Marine Bacteria and Identification of the Key Gene in this Process PDF Nature Microbiology 2 5 17009 doi 10 1038 nmicrobiol 2017 9 PMID 28191900 S2CID 21460292 Ledyard Kathleen M Delong Edward F Dacey John W H 1993 Characterization of a DMSP degrading bacterial isolate from the Sargasso Sea Archives of Microbiology 160 4 312 318 doi 10 1007 bf00292083 S2CID 33566366 Yoch D C 2002 Dimethylsulfoniopropionate Its sources role in the marine food web and biological degradation to dimethylsulfide Applied and Environmental Microbiology 68 12 5804 15 Bibcode 2002ApEnM 68 5804Y doi 10 1128 aem 68 12 5804 5815 2002 PMC 134419 PMID 12450799 DMS The Climate Gas You ve Never Heard of Nakajima Kenji 1996 Effects of DMSP and Related Compounds on Behavior Growth and Stress Resistance of Fish Amphibians and Crustaceans in Kiene R P Visscher P T Keller M D Kirst G O eds Biological and Environmental Chemistry of DMSP and Related Sulfonium Compounds Springer Boston MA pp 165 176 doi 10 1007 978 1 4613 0377 0 15 ISBN 9780306453069External links editDMS and Climate Retrieved from https en wikipedia org w index php title Dimethylsulfoniopropionate amp oldid 1170801318, wikipedia, wiki, book, books, library,
