(2S)-2,3-二羟基丙基磷酸二氢酯 | 5746-57-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 中文名称: (2S)-2,3-二羟基丙基磷酸二氢酯
• 英文名称: L-α-Phosphatidic acid
• 英文别名: α-glycerophosphate；sn-glycerol-1-phosphate；(S)-glyceryl phosphate；D-glycerol-3-phosphate；L-glycerol 3-phosphate；glycerol 3-phosphate；[(2S)-2,3-dihydroxypropyl] dihydrogen phosphate
• CAS: 5746-57-6
• 化学式: C₃H₉O₆P
• 分子量: 172.075
• InChiKey: AWUCVROLDVIAJX-VKHMYHEASA-N

物化性质

• 比旋光度：
  D -1.45° (barium salt, c = 10.3 in 2N HCl)
• 沸点：
  485.5±55.0 °C(Predicted)
• 密度：
  1.738±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2,3-二羟基丙基磷酸二氢酯 、 香叶基焦磷酸铵盐 在 PcrB 作用下， 反应 2.0h， 生成 (S,E)-3-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-2-hydroxypropyl dihydrogen phosphate
  参考文献：
  名称：

  细菌中 TIM 桶异戊二烯转移酶的两种不同机制

  摘要：

  研究了两种细菌 TIM 桶异戊二烯转移酶 (PT) MoeO5 和 PcrB 的反应。MoeO5 是莫诺霉素生物合成第一步的酶，它催化法呢基向 3-磷酸甘油酸 (3PG) 的转移，得到含有顺式烯丙基双键的产物。我们表明该反应涉及异构化为橙花酸焦磷酸中间体，然后在亲核试剂攻击之前进行键旋转。这种机制对于催化分子间偶联的异戊二烯转移酶来说是前所未有的。我们还表明 PcrB 将香叶基和香叶基香叶基转移到 1-磷酸甘油 (G1P)，使其成为第一个使用 G1P 作为底物的已知细菌酶。与 MoeO5 不同，PcrB 无需异构化即可催化异戊二烯转移，生成保留异戊二烯供体的反式烯丙基键的产物。

  DOI：

  10.1021/ja109578b
• 作为产物：
  描述：

  3-溴-1,2-并二酚 在 吡啶 、 三氯氧磷 作用下， 生成 (2S)-2,3-二羟基丙基磷酸二氢酯
  参考文献：
  名称：

  Abderhalden; Eichwald, Chemische Berichte, 1918, vol. 51, p. 1318

  摘要：

  DOI：

文献信息

• An efficient chemoenzymatic route to dihydroxyacetone phosphate from glycidol for the in situ aldolase-mediated synthesis of monosaccharides
  作者：Franck Charmantray、Phillipe Dellis、Soth Samreth、Laurence Hecquet

  DOI：10.1016/j.tetlet.2006.03.036

  日期：2006.5

  We report a new two-step procedure that uses inexpensive rac-glycidol to obtain valuable dihydroxyacetone phosphate (DHAP), a building block for the synthesis of monosaccharide analogues.

  我们报告了一个新的两步程序，该程序使用廉价的rac-缩水甘油来获得有价值的磷酸二羟基丙酮磷酸酯（DHAP），这是合成单糖类似物的基础。
• Biosynthesis of archaebacterial ether lipids. Formation of ether linkages by prenyltransferases
  作者：Donglu Zhang、C. Dale Poulter

  DOI：10.1021/ja00057a008

  日期：1993.2

  Biosynthesis of (R)-2,3-di-O-phytanylglycerol (1), the core lipid of the membranes in the strict anaerobe Methanobacterium thermoautotrophicum, was studied in cell-free preparation. Two prenyltransferase activities were separated by ultracentrifugation. The cytosolic fraction contained activity for (S)-3-O-geranylgeranylglyceryl phosphate synthase (CGGP synthase), which catalyzes alkylation of (S)-glyceryl

  在无细胞制备中研究了 (R)-2,3-di-O-phytanylglycerol (1) 的生物合成，这是严格厌氧型嗜热自养甲烷杆菌膜的核心脂质。通过超速离心分离两种异戊二烯基转移酶活性。胞质部分含有 (S)-3-O-香叶基香叶基甘油基磷酸合酶 (CGGP 合酶) 的活性，该酶催化 (S)-甘油基磷酸酯 [(S)-3-OP] 被香叶基香叶基二磷酸 (5-OPP) 烷基化，而颗粒含有 (S)-2,3-O-二香叶基香叶基甘油基磷酸合酶 (DGGGP 合酶) 的活性，该酶催化 (S)-3-O-香叶基香叶基甘油基磷酸酯 [(S)-12-OP] 通过 5-奥普
• Identification of<i>sn</i>-Glycerol-1-phosphate Dehydrogenase Activity from Genomic Information on a Hyperthermophilic Archaeon,<i>Sulfolobus tokodaii</i>Strain 7
  作者：Yosuke KOGA、Mami OHGA、Masanari TSUJIMURA、Hiroyuki MORII、Yutaka KAWARABAYASI

  DOI：10.1271/bbb.70.282

  日期：2006.1

  sn-Glycerol-1-phosphate dehydrogenase is responsible for the formation of sn-glycerol-1-phosphate, the backbone of membrane phospholipids of Archaea. This activity had never been detected in cell-free extract of Sulfolobus sp. Here we report the detection of this activity on the thermostable ST0344 protein of Sulfolobus tokodaii expressed in Escherichia coli, which was predicted from genomic information on S. tokodaii. This is another line of evidence for the general mechanism of sn-glycerol-1-phosphate formation by the enzyme.

  sn-1-磷酸甘油脱氢酶负责形成 sn-1-磷酸甘油，古细菌膜磷脂的骨架。在硫化叶菌的无细胞提取物中从未检测到这种活性。在这里，我们报告了在大肠杆菌中表达的托科代硫化叶菌的热稳定性 ST0344 蛋白上检测到的这种活性，这是根据托科代硫化叶菌的基因组信息预测的。这是该酶形成 sn-甘油-1-磷酸一般机制的另一条证据。
• Synthesis and hydrolytic stability of cyclic phosphatidic acids: implications for synthetic- and proto-cell studies
  作者：Veronica Egas Ortuno、Sunil Pulletikurti、Kollery S. Veena、Ramanarayanan Krishnamurthy

  DOI：10.1039/d2cc00292b

  日期：——

  Cyclic phosphatidic acids (cPAs) are bioactive compounds with therapuetic potential, but are in short supply. We describe a robust synthesis of cPAs employing an efficient cyclophosphorylation procedure and report on their hydrolytic properties – which should facilitate the study of their biological properties and as plausible proto- and synthetic-cell components.

  环磷脂酸 (cPA) 是具有治疗潜力的生物活性化合物，但供不应求。我们描述了采用有效的环磷酸化程序的 cPA 的稳健合成，并报告了它们的水解特性——这应该有助于研究它们的生物学特性以及作为合理的原始细胞和合成细胞成分。
• One-pot enzymatic reaction sequence for the syntheses of d-glyceraldehyde 3-phosphate and l-glycerol 3-phosphate
  作者：Getachew S. Molla、Roland Wohlgemuth、Andreas Liese

  DOI：10.1016/j.molcatb.2015.12.004

  日期：2016.2

  A one-pot enzymatic reaction sequence for the synthesis of optically pure D-glyceraldehyde 3-phosphate (D-GAP) and L-glycerol 3-phosphate (sn-G3P) was designed using fructose-bisphosphate aldolase from rabbit muscle (RAMA), sn-glycerol 3-phosphate dehydrogenase (sn-G3PDH) and formate dehydrogenase from Candida boidinii (FDH). The reaction sequence significantly improves the aldol cleavage of D-fructose 1,6-bisphosphate (D-F16BP) catalyzed by RAMA and yields 100% conversion of D-F16BP by overcoming thermodynamic limitation. The degradation kinetics of D-GAP under reaction conditions was investigated and a reaction kinetics model defining the entire cascade was developed. Validation of the model shows 98.5% correlation between experimental data and numerically simulated data matrices. The evaluation of different types of reactor was performed by combining the reaction kinetics model, mass balances and kinetics of the non-enzymatic degradation of D-GAP. Batch-wise operation in a stirred tank reactor (STR) is the most convenient procedure for the one-pot enzymatic syntheses of D-GAP and sn-G3P. The separation of the two products D-GAP and sn-G3P has been achieved using polyethylenimine (PEI)-cellulose TLC. (C) 2015 Elsevier B.V. All rights reserved.