(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol | 608880-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol
• 英文别名: [(E,2S,3R)-3-benzoyloxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-14-[4-(2,2,2-trifluoroacetyl)phenoxy]tetradec-4-enyl] benzoate
• CAS: 608880-41-7
• 化学式: C₄₁H₄₈F₃NO₈
• 分子量: 739.829
• InChiKey: PZINSBAAHTXJDX-UDBYFYABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  53
• 可旋转键数：
  24
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol 在 吡啶 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以99%的产率得到(2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol oxime
  参考文献：
  名称：

  Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate:  Differential Interaction with Protein Targets

  摘要：

  The first synthesis of two photoreactive analogues of the lipid mediator and second messenger sphingosine 1-phosphate (S1P), [P-32]-labeled (2S,3R)-14-O-(4'-benzoylphenyl)- and (2S,3R)-14-O-((4'-trifluoromethyldiazirinyl)phenyl)-(4E)-tetradecenyl-2-amino-3-hydroxy-1-phosphate, is described. The interactions of these probes with the SIP type-1 receptor (S1P(1)) transfected into membranes of rat hepatoma cells and with plasma proteins were analyzed. The S1P(1) receptor interacted in a specific manner with the benzophenone-containing ligand (K-D = 84 +/- 10 nM vs K-D for S1P = 36 +/- 2 nM); in contrast, no saturable specific binding was found with the diazirine-containing ligand. However, the same pattern was found for labeling of plasma proteins by both probes, indicating that different parts of the SIP pharmacophore underlie the interaction of S1P with its receptor and plasma carrier proteins.

  DOI：

  10.1021/jo034828q
• 作为产物：
  描述：

  2,2,2-三氟-4-甲氧基乙酰苯 在 偶氮二甲酸二异丙酯 、 三苯基膦 、 lithium chloride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2S,3R)-1,3-di-O-benzoyl-2-(tert-butoxycarbonylamino)-14-O-(4'-(trifluoroacetyl)phenyl)-(4E)-tetradecene-1,3,14-triol
  参考文献：
  名称：

  Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate:  Differential Interaction with Protein Targets

  摘要：

  The first synthesis of two photoreactive analogues of the lipid mediator and second messenger sphingosine 1-phosphate (S1P), [P-32]-labeled (2S,3R)-14-O-(4'-benzoylphenyl)- and (2S,3R)-14-O-((4'-trifluoromethyldiazirinyl)phenyl)-(4E)-tetradecenyl-2-amino-3-hydroxy-1-phosphate, is described. The interactions of these probes with the SIP type-1 receptor (S1P(1)) transfected into membranes of rat hepatoma cells and with plasma proteins were analyzed. The S1P(1) receptor interacted in a specific manner with the benzophenone-containing ligand (K-D = 84 +/- 10 nM vs K-D for S1P = 36 +/- 2 nM); in contrast, no saturable specific binding was found with the diazirine-containing ligand. However, the same pattern was found for labeling of plasma proteins by both probes, indicating that different parts of the SIP pharmacophore underlie the interaction of S1P with its receptor and plasma carrier proteins.

  DOI：

  10.1021/jo034828q

文献信息

• Total Synthesis of Two Photoactivatable Analogues of the Growth-Factor-Like Mediator Sphingosine 1-Phosphate:  Differential Interaction with Protein Targets
  作者：Xuequan Lu、Sandor Cseh、Hoe-Sup Byun、Gabor Tigyi、Robert Bittman

  DOI：10.1021/jo034828q

  日期：2003.9.1

  The first synthesis of two photoreactive analogues of the lipid mediator and second messenger sphingosine 1-phosphate (S1P), [P-32]-labeled (2S,3R)-14-O-(4'-benzoylphenyl)- and (2S,3R)-14-O-((4'-trifluoromethyldiazirinyl)phenyl)-(4E)-tetradecenyl-2-amino-3-hydroxy-1-phosphate, is described. The interactions of these probes with the SIP type-1 receptor (S1P(1)) transfected into membranes of rat hepatoma cells and with plasma proteins were analyzed. The S1P(1) receptor interacted in a specific manner with the benzophenone-containing ligand (K-D = 84 +/- 10 nM vs K-D for S1P = 36 +/- 2 nM); in contrast, no saturable specific binding was found with the diazirine-containing ligand. However, the same pattern was found for labeling of plasma proteins by both probes, indicating that different parts of the SIP pharmacophore underlie the interaction of S1P with its receptor and plasma carrier proteins.