Dimethyl sulfonium propionate
| Structural formula | ||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
||||||||||||||||
| General | ||||||||||||||||
| Surname | Dimethyl sulfonium propionate | |||||||||||||||
| other names |
|
|||||||||||||||
| Molecular formula | C 5 H 10 O 2 S | |||||||||||||||
| Brief description |
white, crystalline, hygroscopic powder with a characteristic odor |
|||||||||||||||
| External identifiers / databases | ||||||||||||||||
|
||||||||||||||||
| properties | ||||||||||||||||
| Molar mass | 134.1967 g mol −1 | |||||||||||||||
| Physical state |
firmly |
|||||||||||||||
| Melting point |
120-125 ° C |
|||||||||||||||
| safety instructions | ||||||||||||||||
|
||||||||||||||||
| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Dimethyl sulfoniopropionate (often abbreviated as DMSP) is an organosulfur compound . This zwitterionic metabolite is found in marine phytoplankton , seaweed, and some species of terrestrial and aquatic vascular plants . It acts as an osmolyte and plays a role in physiological and environmental aspects.
biosynthesis
In higher plants, DMSP is biosynthesized from S -methyl methionine. Two intermediate products are dimethylsulfonium propylamine and dimethylsulfonium propionaldehyde. In algae, however, biosynthesis starts with the splitting off of the amino group from methionine instead of S- methyl methionine .
Degradation
DMSP is broken down by marine microbes into volatile sulfur compounds, each of which has specific effects on the environment. The main breakdown product is methanethiol (CH 3 SH), which is converted into sulfur proteins by bacteria. The second volatile degradation product is dimethyl sulfide (CH 3 SCH 3 ; DMS). Most of the DMS in seawater is split off from DMSP by the enzyme DMSP lyase . In contrast, many non-marine bacteria convert methanethiol into DMS.
DMS is also taken up by marine bacteria, but not as quickly as methanethiol. Although DMS only accounts for around 25% of the volatile breakdown products of DMSP, the high reactivity of methanethiol means that the DMS concentration in seawater is ten times higher (around 3 nM ). Much of the DMS in seawater is oxidized to dimethyl sulfoxide (DMSO).
DMS is believed to play a role in the earth's heat balance by reducing the amount of solar radiation that can reach the earth's surface.
DMSP is attributed to affecting the taste and smell of various products. It is highly enriched by some marine herbivores and filter feeders , for example . DMS, in turn, is responsible for the disgusting taste and smell of some seafood due to the reaction of DMSP lyase in the bacteria, which also creates acrylates .
See also
- CLAW hypothesis assumes that phytoplankton play an important role in the earth's climate system
- Haptophyta , an order of marine, unicellular algae that produce DMSP
- Dimethyl sulfide , a cleavage product of DMSP, together with methanethiol
- Dimethyl selenide , a selenium analogue of dimethyl sulfide, produced by bacteria and phytoplankton
- Emiliania huxleyi , a calcareous alga of the order Haptophyta that produces DMSP
Web links
- DMS and Climate ( Memento from February 14, 2015 in the Internet Archive )
Individual evidence
- ↑ a b tianyuchem: Dimethylpropiothetin ( memento of the original from March 6, 2013 in the web archive archive.today ) Info: The archive link was automatically inserted and not yet checked. Please check the original and archive link according to the instructions and then remove this notice.
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Jennifer L. DeBose, Sean C. Lema, Gabrielle A. Nevitt: Dimethylsulfoniopropionate as a foraging cue for reef fishes . (abstract) In: Science . 319, No. 5868, March 7, 2008, p. 1356. doi : 10.1126 / science.1151109 . PMID 18323445 . Retrieved March 21, 2008. Maria Vila-Costa, Rafel Simo, Hyakubun Harada, Josep M. Gasol, Doris Slezak, Ronald P. Kiene: Dimethylsulfoniopropionate uptake by marine phytoplankton . (abstract) In: Science . 314, No. 5799, October 27, 2006, pp. 652-654. doi : 10.1126 / science.1131043 . PMID 17068265 . Retrieved March 21, 2008.
- ↑ Scott D. McNeil, Michael L. Nuccio, Andrew D. Hanson: Betaines and Related Osmoprotectants. Targets for Metabolic Engineering of Stress Resistance . In: Plant Physiology , August 1999, Vol. 120, pp. 945-949, doi: 10.1104 / pp.120.4.945 .
- ↑ Naomi Marcil Levine, Vanessa A. Varaljay, Dierdre A. Toole, John WH Dacey, Scott C. Doney, Mary Ann Moran: Environmental, biochemical and genetic drivers of DMSP degradation and DMS production in the Sargasso Sea. In: Environmental Microbiology. 14, 2012, pp. 1210-1223, doi: 10.1111 / j.1462-2920.2012.02700.x .
- ↑ Martí Galí, Rafel Simó: Occurrence and cycling of dimethylated sulfur compounds in the Arctic during summer receding of the ice edge . (PDF) In: Marine Chemistry , Volume 122, Issue 1–4, October 2010, pp. 105–117 (English). Also: doi: 10.1016 / j.marchem.2010.07.003 , July 24, 2010.
- ↑ Dimethyl sulfide emission: Climate Control by Marine Algae . ProQuest.
- ↑ Hannah Lutterbeck: The distribution of DMS / DMSP / DMSO during the SOPRAN mesocosm experiment 2011 in Bergen (Norway) . (PDF; 22.9 MB) Diploma thesis, February 2012.
- ↑ Biological and Environmental Chemistry of DMSP and Related Sulfonium Compounds , 1996, pp. 265-276, Metabolic Pathways Involved in DMSP Degradation, doi : 10.1007 / 978-1-4613-0377-0_23 .
