2-(1',2'-O-di-n-hexanoyl-sn-3'-glyceryl)-2-thio-1,3,2-dithiaphospholane | 151600-62-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(1',2'-O-di-n-hexanoyl-sn-3'-glyceryl)-2-thio-1,3,2-dithiaphospholane
• 英文别名: 2-O-(1,2-di-n-hexanoyl-sn-3-glyceryl)-2-thio-1,3,2-dithiophospholane；[(2R)-2-hexanoyloxy-3-[(2-sulfanylidene-1,3,2lambda5-dithiaphospholan-2-yl)oxy]propyl] hexanoate；[(2R)-2-hexanoyloxy-3-[(2-sulfanylidene-1,3,2λ5-dithiaphospholan-2-yl)oxy]propyl] hexanoate
• CAS: 151600-62-3
• 化学式: C₁₇H₃₁O₅PS₃
• 分子量: 442.602
• InChiKey: ZVGJLPUSMUWUOL-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(1',2'-O-di-n-hexanoyl-sn-3'-glyceryl)-2-thio-1,3,2-dithiaphospholane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 8.5h， 生成
  参考文献：
  名称：

  A general and efficient route to phosphorodithioate analogs of naturally occurring lipids

  摘要：

  A general procedure has been developed for the efficient synthesis of lipid phosphorodithioate analogues 14a-f from 2-alkoxy-2-thio-1,3,2-dithiaphospholanes 13a-c, which are readily prepared from 2-chloro-1,3,2-dithiaphospholane (11) by sequential reaction with an alcohol and elemental sulfur.

  DOI：

  10.1021/jo00074a012
• 作为产物：
  描述：

  1,2-二己酰-Sn-甘油 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 N,N-二异丙基乙胺 作用下， 以 二硫化碳 、 乙腈 为溶剂， 反应 9.0h， 生成 2-(1',2'-O-di-n-hexanoyl-sn-3'-glyceryl)-2-thio-1,3,2-dithiaphospholane
  参考文献：
  名称：

  A general and efficient route to phosphorodithioate analogs of naturally occurring lipids

  摘要：

  A general procedure has been developed for the efficient synthesis of lipid phosphorodithioate analogues 14a-f from 2-alkoxy-2-thio-1,3,2-dithiaphospholanes 13a-c, which are readily prepared from 2-chloro-1,3,2-dithiaphospholane (11) by sequential reaction with an alcohol and elemental sulfur.

  DOI：

  10.1021/jo00074a012

文献信息

• Synthesis and Kinetic Evaluation of Inhibitors of the Phosphatidylinositol-Specific Phospholipase C from <i>Bacillus cereus</i>
  作者：Stephen F. Martin、Allan S. Wagman

  DOI：10.1021/jo960850q

  日期：1996.11.15

  Substrate analogues of phosphatidylinositol (1) were synthesized and evaluated as potential inhibitors of the bacterial phosphatidylinositol-specific phospholipase C (PI-PLC) from Bacillus cereus. The chiral analogues of the water-soluble phospholipid substrate 5 were designed to probe the effects of varying the inositol C-2 hydroxyl group, which is generally believed to serve as the nucleophile in

  合成了磷脂酰肌醇（1）的底物类似物，并评估为蜡状芽孢杆菌的细菌磷脂酰肌醇特异性磷脂酶C（PI-PLC）的潜在抑制剂。水溶性磷脂底物5的手性类似物被设计成探测改变肌醇C-2羟基的作用，通常认为它通过PI-PLC在磷脂酰肌醇水解的第一步中用作亲核试剂。在类似物6-9中，磷脂酰肌醇衍生物的肌醇环上的C-2羟基以几种方式被合理地改变。肌醇环C-2处的立体化学颠倒导致了scyllo衍生物6。肌醇C-2羟基被氟取代，以产生烷基-氟代肌醇7，氢原子被取代以提供2-脱氧化合物8。C-2羟基被O-甲基化以制备甲氧基衍生物9. C-2处的天然肌醇构型保留在不可水解的二硫代磷酸酯类似物10中。然后使用D-肌醇1-（4-硝基苯基）在连续测定法中分析这些类似物对PI-PLC的抑制作用（25）作为发色底物。确定了每种磷脂酰肌醇衍生物的动力学参数，发现它们是具有K（i）的竞争性抑制剂，如下：6,0.2mM; 10，0.6毫米;
• Design, Synthesis, and Evaluation of Phospholipid Analogs as Inhibitors of the Bacterial Phospholipase C from Bacillus cereus
  作者：Stephen F. Martin、Yue-Ling Wong、Allan S. Wagman

  DOI：10.1021/jo00096a024

  日期：1994.8

  Enzymes belonging to the phospholipase C (PLC) family hydrolyze the phosphodiester bond of phospholipids to give a diacylglycerol and a phosphorylated head group. The bacterial phospholipase C from Bacillus cereus (PLC(Bc)) has been studied extensively, and there is a wealth of information regarding those structural features that are important for substrate activity. In contrast, there is virtually no data available regarding structure-activity relationships for inhibitors of this enzyme. To address this shortcoming, a series of optically pure analogues of 1,2-dihexanoyl-sn-glycero-3-phosphocholine (2) containing different replacements of the phosphate group were first synthesized including the phosphoramidates 4 and 8, the phosphonate 5, the (difluoromethylene)phosphonate 6, the thiophosphate 7, the diastereomeric phosphorothioates 9 and 10, and the phosphorodithioate 11. Each of these phosphatidylcholine derivatives was tested for inhibitor or substrate activity with PLC(Bc) using the water-soluble phosphatidylcholine 2 as the monomeric substrate. The measurements were conducted below the critical micellar concentrations of both 2 and the inhibitor. Of the analogues, only 7 and 9 underwent observable enzymatic hydrolysis under the assay conditions used. The k(cat) of the (Sp)-phosphorothioate 9 was approximately one-fifth that of 2, and when compared to 2, 7 was hydrolyzed only very slowly by the enzyme. Kinetic studies indicated that the phospholipid analogues tested were competitive inhibitors with increasing K-i's follows: 7 approximate to 11 approximate to 10 < 4 approximate to 8 < 5 approximate to 6.