1,2-di-n-hexanoyl-sn-glycero-3-phosphodithiocholine

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油-3-二硫代磷酸胆碱
• 英文名称: 1,2-di-n-hexanoyl-sn-glycero-3-phosphodithiocholine
• 英文别名: 2-[[(2R)-2,3-di(hexanoyloxy)propoxy]-sulfidophosphinothioyl]oxyethyl-trimethylazanium
• 化学式: C₂₀H₄₀NO₆PS₂
• 分子量: 485.646
• InChiKey: XCEGGJVDIANRGJ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 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 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 作用下， 以 二硫化碳 、 乙腈 为溶剂， 反应 9.5h， 生成 1,2-di-n-hexanoyl-sn-glycero-3-phosphodithiocholine
  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

• A general and efficient route to phosphorodithioate analogs of naturally occurring lipids
  作者：Stephen F. Martin、Allan S. Wagman

  DOI：10.1021/jo00074a012

  日期：1993.10

  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.
• 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.