Dimethylsulfoniopropionate
Names | |
---|---|
IUPAC name
3-dimethylsulfoniopropanoate
| |
Other names
dimethyl-β-propiothetin
S,S-dimethyl-β-propiothetin | |
Identifiers | |
3D model (
JSmol ) |
|
ChemSpider | |
ECHA InfoCard
|
100.228.826 |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C5H10O2S | |
Molar mass | 134.1967 |
Appearance | 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).
|
Dimethylsulfoniopropionate (DMSP), is an
Polysiphonia fastigiata.[4]
Biosynthesis
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]
Degradation
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
DMSP-lyase, although many non-marine species of bacteria convert methanethiol to DMS.[citation needed
]
DMS is also taken up by
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
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
seafood products because of the action of bacterial DMSP-lyase, which cogenerates acrylate
.
Further reading
- 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. ISBN 978-3-319-07144-2.
See also
- 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
- 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 DMSP
References
- ^ "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.
- S2CID 27541024.
- PMID 18101461.
- PMID 10444077.
- S2CID 21460292.
- S2CID 33566366.
- PMID 12450799.
- ^ "DMS: The Climate Gas You've Never Heard of".
- ISBN 9780306453069