二甲基巰基丙酸

二甲基巰基丙酸
IUPAC名 (Dimethylsulfaniumyl)propanoate
別名	dimethyl-β-propiothetin
識別
CAS號	7314-30-9  Y
PubChem	23736
ChemSpider	22195
SMILES	C[S+](C)CCC(=O)[O-]
InChI	1/C5H10O2S/c1-8(2)4-3-5(6)7/h3-4H2,1-2H3
InChIKey	DFPOZTRSOAQFIK-UHFFFAOYAW
性質
化學式	C5H10O2S
莫耳質量	134.1967 g·mol⁻¹
外觀	white crystalline powder with hygroscopicity and characteristic odor.
熔點	120 - 125 °C
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

二甲基巰基丙酸（英語：Dimethylsulfoniopropionate，縮寫DMSP）是一種化學式為(CH₃)₂S⁺CH₂CH₂COO⁻的有機化合物，常以內鹽形式存在於海洋浮游植物、海藻以及某些陸生及水生維管植物中。

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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)

生物合成

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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.

降解

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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 methanethiol (CH₃SH), which is assimilated by bacteria into protein sulfur. Its second volatile breakdown product is dimethyl sulfide (CH₃SCH₃; DMS). Most DMS in seawater is cleaved from 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).

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.

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. 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.

外部連結

• DMS and Climate