(R)-2,3-bis(hexadecyloxy)propyl 4-methylbenzenesulfonate | 1221430-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2,3-bis(hexadecyloxy)propyl 4-methylbenzenesulfonate
• 英文别名: [(2R)-2,3-dihexadecoxypropyl] 4-methylbenzenesulfonate
• CAS: 1221430-17-6
• 化学式: C₄₂H₇₈O₅S
• 分子量: 695.144
• InChiKey: DTWBWWACYDQKAZ-VQJSHJPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.8
• 重原子数：
  48
• 可旋转键数：
  37
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2,3-bis(hexadecyloxy)propyl 4-methylbenzenesulfonate 在 碘 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以88%的产率得到(R)-1-(1-(hexadecyloxy)-3-iodopropan-2-yloxy)hexadecane
  参考文献：
  名称：

  Structure−Activity Relationships in Toll-like Receptor-2 Agonistic Diacylthioglycerol Lipopeptides

  摘要：

  The N-termini of bacterial lipoproteins are acylated with a (S)-(2,3-bisacyloxypropyl)cysteinyl residue. Lipopeptides derived from lipoproteins activate innate immune responses by engaging Toll-like receptor 2 (TLR2) and are highly immunostimulatory and yet without apparent toxicity in animal models. The lipopeptides may therefore be useful as potential immunotherapeutic agents. Previous structure activity relationships in such lipopeptides have largely been obtained using murine cells, and it is now clear that significant species-specific differences exist between human and murine TLR responses. We have examined in detail the role of the highly conserved Cys residue as well as the geometry and stereochemistry of the Cys-Ser dipeptide unit. (R)-Diacylthioglycerol analogues are maximally active in reporter gene assays using human TLR2. The Cys-Ser dipeptide unit represents the minimal part-structure, but its stereochemistry was found not to be a critical determinant of activity. The thioether bridge between the diacyl and dipeptide units is crucial, and replacement by an oxoether bridge results in a dramatic decrease in activity.

  DOI：

  10.1021/jm901839g
• 作为产物：
  描述：

  对甲苯磺酰氯 、 1,2-o-二十六基-sn-甘油 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以527 mg的产率得到(R)-2,3-bis(hexadecyloxy)propyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Structure−Activity Relationships in Toll-like Receptor-2 Agonistic Diacylthioglycerol Lipopeptides

  摘要：

  The N-termini of bacterial lipoproteins are acylated with a (S)-(2,3-bisacyloxypropyl)cysteinyl residue. Lipopeptides derived from lipoproteins activate innate immune responses by engaging Toll-like receptor 2 (TLR2) and are highly immunostimulatory and yet without apparent toxicity in animal models. The lipopeptides may therefore be useful as potential immunotherapeutic agents. Previous structure activity relationships in such lipopeptides have largely been obtained using murine cells, and it is now clear that significant species-specific differences exist between human and murine TLR responses. We have examined in detail the role of the highly conserved Cys residue as well as the geometry and stereochemistry of the Cys-Ser dipeptide unit. (R)-Diacylthioglycerol analogues are maximally active in reporter gene assays using human TLR2. The Cys-Ser dipeptide unit represents the minimal part-structure, but its stereochemistry was found not to be a critical determinant of activity. The thioether bridge between the diacyl and dipeptide units is crucial, and replacement by an oxoether bridge results in a dramatic decrease in activity.

  DOI：

  10.1021/jm901839g

文献信息

• Structure−Activity Relationships in Toll-like Receptor-2 Agonistic Diacylthioglycerol Lipopeptides
  作者：Wenyan Wu、Rongti Li、Subbalakshmi S. Malladi、Hemamali J. Warshakoon、Matthew R. Kimbrell、Michael W. Amolins、Rehman Ukani、Apurba Datta、Sunil A. David

  DOI：10.1021/jm901839g

  日期：2010.4.22

  The N-termini of bacterial lipoproteins are acylated with a (S)-(2,3-bisacyloxypropyl)cysteinyl residue. Lipopeptides derived from lipoproteins activate innate immune responses by engaging Toll-like receptor 2 (TLR2) and are highly immunostimulatory and yet without apparent toxicity in animal models. The lipopeptides may therefore be useful as potential immunotherapeutic agents. Previous structure activity relationships in such lipopeptides have largely been obtained using murine cells, and it is now clear that significant species-specific differences exist between human and murine TLR responses. We have examined in detail the role of the highly conserved Cys residue as well as the geometry and stereochemistry of the Cys-Ser dipeptide unit. (R)-Diacylthioglycerol analogues are maximally active in reporter gene assays using human TLR2. The Cys-Ser dipeptide unit represents the minimal part-structure, but its stereochemistry was found not to be a critical determinant of activity. The thioether bridge between the diacyl and dipeptide units is crucial, and replacement by an oxoether bridge results in a dramatic decrease in activity.