二甲基丙酸噻亭 | 7314-30-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 二甲基丙酸噻亭
• 中文别名: 硫代甜菜碱
• 英文名称: dimethylsulfoniopropionate
• 英文别名: DMSP；dimethyl-β-propiothetin；Dimethylpropiothetin；3-dimethylsulfoniopropanoate
• CAS: 7314-30-9
• 化学式: C₅H₁₀O₂S
• mdl: MFCD11100561
• 分子量: 134.199
• InChiKey: DFPOZTRSOAQFIK-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于甲醇、水

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2942000000

制备方法与用途

Dimethylsulfonioproprionate (DMSP) is a metabolite primarily produced by marine phytoplankton and serves as the main precursor to dimethylsulfide (DMS), a climatically important gas. DMSP and DMS are key sources of sulfur aerosols in Earth's atmosphere, potentially influencing global temperature.

反应信息

• 作为反应物：
  描述：

  二甲基丙酸噻亭 在 e^1-_aq 作用下， 生成
  参考文献：
  名称：

  Bonifacic, Marija; Anklam, Elke, Journal of the Chemical Society. Perkin transactions II, 1991, # 2, p. 243 - 248

  摘要：

  DOI：
• 作为产物：
  描述：

  (2-羧乙基)二甲基氯化锍 在 碳酸氢钠 作用下， 以 水 为溶剂， 以80 g的产率得到二甲基丙酸噻亭
  参考文献：
  名称：

  二甲基-β-丙酸噻亭的制备方法

  摘要：

  本发明涉及一种二甲基‑β‑丙酸噻亭的制备方法，涉及有机化学技术领域，本发明采用两步合成方法，首先利用氯丙酸和二甲基硫醚制备β‑二甲基锍基丙酸氯化物，然后加入碳酸氢钠反应后重结晶并干燥，即获得二甲基‑β‑丙酸噻亭（DMPT）；本发明采用独特的合成方法，第一步合成的中间产物收率在65%‑84%，经提纯后产物DMPT纯度可达96%，纯度高，合成步骤简单，宜于推广应用。

  公开号：

  CN107382802A

文献信息

• Sulfonium Acids Loaded onto an Unusual Thiotemplate Assembly Line Construct the Cyclopropanol Warhead of a <i>Burkholderia</i> Virulence Factor
  作者：Felix Trottmann、Keishi Ishida、Jakob Franke、Aleksa Stanišić、Mie Ishida‐Ito、Hajo Kries、Georg Pohnert、Christian Hertweck

  DOI：10.1002/anie.202003958

  日期：2020.8.3

  Pathogenic bacteria of the Burkholderia pseudomallei group cause severe infectious diseases such as glanders and melioidosis. Malleicyprols were identified as important bacterial virulence factors, yet the biosynthetic origin of their cyclopropanol warhead has remained enigmatic. By a combination of mutational analysis and metabolomics we found that sulfonium acids, dimethylsulfoniumpropionate (DMSP)

  假伯克霍尔德氏菌的致病菌该组引起严重的传染病，例如腺体和类瘤病。Malleicyprols被确定为重要的细菌毒力因子，但其环丙醇战斗部的生物合成起源仍是一个谜。通过突变分析和代谢组学的结合，我们发现sulf酸，丙二酸二甲基ulf（DMSP）和go香酚，是渗透压剂，是全球有机硫循环中的关键成分，是通往环丙醇装置的关键中间体。功能遗传学和体外分析揭示了一种涉及稀有甲基化的，涉及罕见的原核SET域甲基转移酶的DMSP专门途径，并表明DMSP通过专用于两性离子起始剂单元的腺苷酸化域被加载到NRPS-PKS杂化装配线上。然后，大合酶将DMSP转化为凉拌酚，大肠杆菌。
• Structure and unimolecular chemistry of protonated sulfur betaines, (CH3)2S+(CH2)nCO2H (n = 1 and 2)
  作者：Ellie Jung-Hwa Yoo、Linda Feketeová、George N. Khairallah、Jonathan M. White、Richard A. J. O'Hair

  DOI：10.1039/c0ob00770f

  日期：——

  The fixed charge zwitterionic sulfur betaines dimethylsulfonioacetate (DMSA) (CH3)2S+CH2CO2− and dimethylsulfoniopropionate (DMSP) (CH3)2S+(CH2)2CO2− have been synthesized and the structures of their protonated salts (CH3)2S+CH2CO2H⋯Cl− [DMSA.HCl] and (CH3)2S+(CH2)2CO2H⋯Pcr− [DMSP.HPcr] (where Pcr = picrate) have been characterized using X-ray crystallography. The unimolecular chemistry of the [M+H]+

  固定电荷两性离子硫甜菜碱 磺基乙酸二甲酯（DMSA）（CH 3）2小号+ CH 2 CO 2 -和丙酸二甲酯（DMSP）（CH 3）2小号+（CH 2）2 CO 2 -已被合成和它们的质子化盐（CH结构3）2小号+ CH 2 CO 2 ħ⋯氯- [DMSA.HCl]和（ CH 3）2小号+（CH 2）2 CO 2 H ^⋯PCR - [DMSP.HPcr]（其中PCR =苦味酸盐），使用X射线晶体学进行了表征。[M + H] +的单分子化学使用两种技术研究了其中的甜菜碱；混合线性离子阱傅里叶变换离子回旋共振质谱仪中的碰撞诱导解离（CID）和电子诱导解离（EID）。CID研究的结果表明，较短链的断裂反应系列更加丰富甜菜碱以及主要的破碎途径形成对比。因此，尽管（CH 3）2 S +（CH 2）2 CO 2 H经由邻近基团反应断裂以产生（CH 3）2 S + H和中性内酯作为最丰富的断裂通道，（CH
• Metabolism of Acrylate to β-Hydroxypropionate and Its Role in Dimethylsulfoniopropionate Lyase Induction by a Salt Marsh Sediment Bacterium, <i>Alcaligenes faecalis</i> M3A
  作者：John H. Ansede、Perry J. Pellechia、Duane C. Yoch

  DOI：10.1128/aem.65.11.5075-5081.1999

  日期：1999.11

  Dimethylsulfoniopropionate (DMSP) is degraded to dimethylsulfide (DMS) and acrylate by the enzyme DMSP lyase. DMS or acrylate can serve as a carbon source for both free-living and endophytic bacteria in the marine environment. In this study, we report on the mechanism of DMSP-acrylate metabolism by Alcaligenes faecalis M3A. Suspensions of citrate-grown cells expressed a low level of DMSP lyase activity that could be induced to much higher levels in the presence of DMSP, acrylate, and its metabolic product, β-hydroxypropionate. DMSP was degraded outside the cell, resulting in an extracellular accumulation of acrylate, which in suspensions of citrate-grown cells was then metabolized at a low endogenous rate. The inducible nature of acrylate metabolism was evidenced by both an increase in the rate of its degradation over time and the ability of acrylate-grown cells to metabolize this molecule at about an eight times higher rate than citrate-grown cells. Therefore, acrylate induces both its production (from DMSP) and its degradation by an acrylase enzyme. ¹ H and ¹³ C nuclear magnetic resonance analyses were used to identify the products resulting from [1- ¹³ C]acrylate metabolism. The results indicated that A. faecalis first metabolized acrylate to β-hydroxypropionate outside the cell, which was followed by its intracellular accumulation and subsequent induction of DMSP lyase activity. In summary, the mechanism of DMSP degradation to acrylate and the subsequent degradation of acrylate to β-hydroxypropionate in the aerobic β-Proteobacterium A. faecalis has been described.

  摘要 二甲基硫代丙酸酯（DMSP）可通过 DMSP 裂解酶降解为二甲基硫醚（DMS）和丙烯酸酯。DMS 或丙烯酸酯可作为海洋环境中自由生活细菌和内生细菌的碳源。在本研究中，我们报告了粪藻菌（Alcaligenes faecalis）代谢 DMSP 丙烯酸酯的机制。 粪钙铝菌 M3A。柠檬酸盐生长的细胞悬浮液表达了低水平的 DMSP 裂解酶活性，在有 DMSP、丙烯酸酯及其代谢产物 β-羟基丙酸酯存在的情况下，这种活性可被诱导到更高的水平。DMSP 在细胞外降解，导致丙烯酸酯在细胞外积累，然后在柠檬酸盐生长的细胞悬浮液中以较低的内源速率进行代谢。丙烯酸酯代谢的诱导性表现在：丙烯酸酯的降解率随着时间的推移而增加，而且丙烯酸酯生长的细胞代谢这种分子的速度比柠檬酸生长的细胞高出约八倍。因此，丙烯酸酯既能诱导其产生（来自 DMSP），也能通过丙烯酸酯酶诱导其降解。 1 H和 13 C 核磁共振分析被用来鉴定由[1- 13 C]acrylate 代谢产生的产物。结果表明 粪肠球菌 首先在细胞外将丙烯酸酯代谢为 β-羟基丙酸酯，然后在细胞内积累，随后诱导 DMSP 裂解酶的活性。总之，在需氧的β-蛋白细菌中，DMSP降解为丙烯酸酯以及随后丙烯酸酯降解为β-羟基丙酸酯的机理如下 A. faecalis 的降解过程。
• The dddP gene of Roseovarius nubinhibens encodes a novel lyase that cleaves dimethylsulfoniopropionate into acrylate plus dimethyl sulfide
  作者：Mark Kirkwood、Nick E. Le Brun、Jonathan D. Todd、Andrew W. B. Johnston

  DOI：10.1099/mic.0.038927-0

  日期：2010.6.1

  The cloneddddPgene of the marine bacteriumRoseovarius nubinhibensallowsEscherichia colito form the volatile dimethyl sulfide (DMS) from dimethylsulfoniopropionate (DMSP), an abundant anti-stress compatible solute made by many marine plankton and macroalgae. Using purified DddP, we show here that this enzyme is a DMSP lyase that cleaves DMSP to DMS plus acrylate. DddP forms a functional homodimeric enzyme, has a pH optimum of 6.0 and was aK_mof ∼14 mM for the DMSP substrate. DddP belongs to the M24B family of peptidases, some members of which have metal cofactors. However, the metal chelators EDTA and bipyridyl did not affect DddP activityin vitroand the as-isolated enzyme did not contain metal ions. Thus, DddP resembles those members of the M24B family, such as creatinase, which also act on a non-peptide substrate and have no metal cofactor. Site-directed mutagenesis of the active-site region of DddP completely abolished its activity. Another enzyme, termed DddL, which occurs in other alphaproteobacteria, had also been shown to generate DMS plus acrylate from DMSP. However, DddL and DddP have no sequence similarity to each other, so DddP represents a second, wholly different class of DMSP lyase.

  海洋细菌Roseovarius nubinhibens的克隆dddP基因使得大肠杆菌能够从丰富的抗压缩溶质二甲基硫代丙酸盐（DMSP）中形成挥发性二甲基硫（DMS）。在使用纯化的DddP时，我们展示了这种酶是一种DMSP裂解酶，可以将DMSP裂解成DMS和丙烯酸。DddP形成一个功能性的同源二聚体酶，pH最适值为6.0，DMSP底物的Km约为14mM。DddP属于肽酶M24B家族，其中一些成员具有金属辅因子。然而，金属螯合剂EDTA和联吡啶对DddP的活性没有影响，而未经处理的酶也不含有金属离子。因此，DddP类似于M24B家族的那些成员，例如肌酸酶，它们也作用于非肽底物并且没有金属辅因子。对DddP的活性位点区域进行定点突变完全消除了其活性。另一种酶称为DddL，在其他α-变形菌中出现，也已被证明能够从DMSP中产生DMS和丙烯酸。然而，DddL和DddP彼此没有序列相似性，因此DddP代表了DMSP裂解酶的第二个完全不同的类别。
• Biochemical, Kinetic, and Spectroscopic Characterization of Ruegeria pomeroyi DddW—A Mononuclear Iron-Dependent DMSP Lyase
  作者：Adam E. Brummett、Nicholas J. Schnicker、Alexander Crider、Jonathan D. Todd、Mishtu Dey

  DOI：10.1371/journal.pone.0127288

  日期：——

  The osmolyte dimethylsulfoniopropionate (DMSP) is a key nutrient in marine environments and its catabolism by bacteria through enzymes known as DMSP lyases generates dimethylsulfide (DMS), a gas of importance in climate regulation, the sulfur cycle, and signaling to higher organisms. Despite the environmental significance of DMSP lyases, little is known about how they function at the mechanistic level. In this study we biochemically characterize DddW, a DMSP lyase from the model roseobacter Ruegeria pomeroyi DSS-3. DddW is a 16.9 kDa enzyme that contains a C-terminal cupin domain and liberates acrylate, a proton, and DMS from the DMSP substrate. Our studies show that as-purified DddW is a metalloenzyme, like the DddQ and DddP DMSP lyases, but contains an iron cofactor. The metal cofactor is essential for DddW DMSP lyase activity since addition of the metal chelator EDTA abolishes its enzymatic activity, as do substitution mutations of key metal-binding residues in the cupin motif (His81, His83, Glu87, and His121). Measurements of metal binding affinity and catalytic activity indicate that Fe(II) is most likely the preferred catalytic metal ion with a nanomolar binding affinity. Stoichiometry studies suggest DddW requires one Fe(II) per monomer. Electronic absorption and electron paramagnetic resonance (EPR) studies show an interaction between NO and Fe(II)-DddW, with NO binding to the EPR silent Fe(II) site giving rise to an EPR active species (g = 4.29, 3.95, 2.00). The change in the rhombicity of the EPR signal is observed in the presence of DMSP, indicating that substrate binds to the iron site without displacing bound NO. This work provides insight into the mechanism of DMSP cleavage catalyzed by DddW.

  海洋环境中一种重要的营养物质——二甲基磺酸丙酸酯（DMSP）——被细菌通过酶（称为DMSP裂解酶）分解，生成二甲基硫醚（DMS）。DMS是一种对气候调节、硫循环和向高等生物发出信号非常重要的气体。尽管DMSP裂解酶对环境意义重大，但人们对它们在机械层面的作用知之甚少。在这项研究中，我们以玫瑰菌属（Roseobacter）的模型菌Ruegeria pomeroyi DSS-3为研究对象，对DMSP裂解酶DddW进行了生化表征。DddW是一种16.9 kDa的酶，含有C端cupin结构域，可从DMSP底物中释放丙烯酸酯、质子和DMS。我们的研究表明，纯化的DddW是一种金属酶，与DddQ和DddP DMSP裂解酶一样，但含有铁辅因子。金属辅因子对DddW DMSP裂解酶的活性至关重要，因为添加金属螯合剂EDTA会消除其酶活性，而cupin结构域中关键的金属结合残基（His81、His83、Glu87和His121）的替代突变也会导致酶活性丧失。对金属结合亲和力和催化活性的测量表明，Fe（II）是最有可能的首选催化金属离子，其结合亲和力为毫摩尔