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Dimethylsulfoniopropionate

Dimethylsulfoniopropionate
Skeletal formula of dimethylsulfoniopropionate
Ball-and-stick model of the dimethylsulfoniopropionate zwitterion
Names
IUPAC name
(Dimethylsulfaniumyl)propanoate
Other names
dimethyl-β-propiothetin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.228.826
PubChem CID
Properties
C5H10O2S
Molar mass 134.1967
Appearance white crystalline hygroscopic powder with a characteristic odor.
Melting point 120 to 125 °C (248 to 257 °F; 393 to 398 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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. DMSP was first identified in the marine red alga Polysiphonia fastigiata by Frederick Challenger and Margaret Simpson (later Dr. Whitaker)

In higher plants, DMSP is biosynthesized from S-methylmethionine. Two intermediates in this conversion are dimethylsulfoniumpropylamine and dimethylsulfoniumpropionaldehyde. In algae, however, the biosynthesis starts with removal of the amino group from methionine, rather than from S-methylmethionine.

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 by the enzyme DMSP-lyase, although many non-marine species of bacteria convert methanethiol to DMS.

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).


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