Phosphoric acid dibenzyl ester (1S,2R,3S,4S,5S,6R)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-hydroxy-cyclohexyl ester | 211869-75-9

• 英文名称: Phosphoric acid dibenzyl ester (1S,2R,3S,4S,5S,6R)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-hydroxy-cyclohexyl ester
• 英文别名: dibenzyl [(1S,2S,3R,4S,5R,6S)-2,4-bis[bis(phenylmethoxy)phosphoryloxy]-5-hydroxy-3,6-bis(phenylmethoxy)cyclohexyl] phosphate
• CAS: 211869-75-9
• 化学式: C₆₂H₆₃O₁₅P₃
• 分子量: 1141.09
• InChiKey: UIGKYQCYBKESLL-LXYFFPQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  80
• 可旋转键数：
  30
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  173
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1,2-di-O-hexadacanoyl-sn-glycerobenzyl (N,N-diisopropylamino)phopshoramidite 、 Phosphoric acid dibenzyl ester (1S,2R,3S,4S,5S,6R)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-hydroxy-cyclohexyl ester 在 四氮唑 、 间氯过氧苯甲酸 作用下， 生成 (+)-1-O-(1,2-di-O-palmitoyl-sn-glycerol-3-benzyloxyphosphoryl)-2,5-di-O-benzyl-3,4,6-tris(dibenzyl phosphate)-myo-inositol
  参考文献：
  名称：

  Molecular Recognition at the Phosphatidylinositol 3,4,5-Trisphosphate-Binding Site. Studies Using the Permuted Isomers of Phosphatidylinositol Trisphosphate

  摘要：

  Permuted isomers of L-alpha-phosphatidyl-D-myo-inositol trisphosphate (PtdInsP(3)), including PtdIns(3,4,5)P-3, PtdIns(3,4,6)P-3, PtdIns(3,5,6)P-3, and PtdIns(4,5,6)P-3, have been synthesized as part of our effort to understand the underlying principles governing ligand selection for Ptdlns(3,4,5)P-3-specific binding proteins. These PtdInsP(3) isomers are examined by using two PtdIns(3,4,5)P-3-dependent functional assays: binding to the C-terminal SH2 domain of the p85 regulatory subunit of PI 3-kinase and platelet aggregation. Our data show that all these isomers bind to the SH2 domain with comparable affinity despite variation in the regioisomeric distribution of phosphate functions. Moreover, all these phospholipids are capable of triggering platelet aggregation with the relative potency of PtdIns(3,4,5)P-3 > PtdIns(3,5,6)P-3 > PtdIns(4,5,6)P-3 > PtdIns(3,4,6)P-3. Evidence suggests that these PtdInsP(3)'s facilitate cell aggregation by activating Ca2+ influx across the plasma membrane. In contrast, other inositol lipids examined including PtdIns(3,4)P-2, PtdIns(4,5)P-2, PtdIns(3)P, and PtdIns(4)P are ineffective in eliciting the aggregation even at much higher concentrations. Taken together, the present data suggest that the charge density on the phosphorylated inositol ring represents a key factor in determining the phosphoinositide binding specificity of target proteins. It is conceivable that the interaction with the PtdIns(3,4,5)P-3-binding motif requires the participation of all three phosphates on the headgroup of PtdIns(3,4,5)P-3. Consequently, other membrane phosphoinositides (e.g., the bis- and monophosphates) become thermodynamically unfavorable for the binding to these PtdIns(3,4,5)P-3 targets.

  DOI：

  10.1021/jo980356h
• 作为产物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 在 四氮唑 、 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 Phosphoric acid dibenzyl ester (1S,2R,3S,4S,5S,6R)-2,5-bis-benzyloxy-3,4-bis-(bis-benzyloxy-phosphoryloxy)-6-hydroxy-cyclohexyl ester
  参考文献：
  名称：

  Molecular Recognition at the Phosphatidylinositol 3,4,5-Trisphosphate-Binding Site. Studies Using the Permuted Isomers of Phosphatidylinositol Trisphosphate

  摘要：

  Permuted isomers of L-alpha-phosphatidyl-D-myo-inositol trisphosphate (PtdInsP(3)), including PtdIns(3,4,5)P-3, PtdIns(3,4,6)P-3, PtdIns(3,5,6)P-3, and PtdIns(4,5,6)P-3, have been synthesized as part of our effort to understand the underlying principles governing ligand selection for Ptdlns(3,4,5)P-3-specific binding proteins. These PtdInsP(3) isomers are examined by using two PtdIns(3,4,5)P-3-dependent functional assays: binding to the C-terminal SH2 domain of the p85 regulatory subunit of PI 3-kinase and platelet aggregation. Our data show that all these isomers bind to the SH2 domain with comparable affinity despite variation in the regioisomeric distribution of phosphate functions. Moreover, all these phospholipids are capable of triggering platelet aggregation with the relative potency of PtdIns(3,4,5)P-3 > PtdIns(3,5,6)P-3 > PtdIns(4,5,6)P-3 > PtdIns(3,4,6)P-3. Evidence suggests that these PtdInsP(3)'s facilitate cell aggregation by activating Ca2+ influx across the plasma membrane. In contrast, other inositol lipids examined including PtdIns(3,4)P-2, PtdIns(4,5)P-2, PtdIns(3)P, and PtdIns(4)P are ineffective in eliciting the aggregation even at much higher concentrations. Taken together, the present data suggest that the charge density on the phosphorylated inositol ring represents a key factor in determining the phosphoinositide binding specificity of target proteins. It is conceivable that the interaction with the PtdIns(3,4,5)P-3-binding motif requires the participation of all three phosphates on the headgroup of PtdIns(3,4,5)P-3. Consequently, other membrane phosphoinositides (e.g., the bis- and monophosphates) become thermodynamically unfavorable for the binding to these PtdIns(3,4,5)P-3 targets.

  DOI：

  10.1021/jo980356h