(2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester | 607358-65-6

• 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: (2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[2-[[(2R,3R)-2,3-dihydroxy-4-[(4-methoxyphenyl)methoxy]butoxy]-phenylmethoxyphosphoryl]oxyethyl]carbamate
• CAS: 607358-65-6
• 化学式: C₂₉H₃₆NO₁₀P
• 分子量: 589.579
• InChiKey: XDPDUEOWIPHRNH-DBQCHVCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  41
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  142
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester 在 四氮唑 、 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 hexadecanoic acid {(1R,2R)-1-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxymethyl]-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-hexanoyloxy}-propyl ester
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a
• 作为产物：
  描述：

  [2-(benzyloxy-diisopropylamino-phosphanyloxy)-ethyl]-carbamic acid benzyl ester 在 四氮唑 、 盐酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Hybrid Lipid Probes:  Derivatives of Phosphatidylethanolamine-Extended Phosphatidylinositol 4,5-Bisphosphate (Pea-PIP₂)

  摘要：

  The total asymmetric synthesis of a novel hybrid lipid possessing a 2,3-diacylthreitol backbone, rather than a 1,2-diacylglycerol backbone, is described. The title compound, Pea-PIP2, possesses a phosphatidylethanolamine (PE) headgroup at the 1-position and a phosphatidylinositol 4,5-bisphosphate (Ptdlns(4,5)P-2) headgroup, at the 4-position. Reporters (biotin, fluorophores, spin label) were covalently attached to the free amino group of the PE, such that these reporters were targeted to the lipid-water interface. The diacyl moieties allow incorporation of Pea-PIP2 into a lipid bilayer, while the PtdIns(4,5)P-2 moiety in the aqueous layer was specifically recognized by PtdIns(4,5)P-2-specific binding proteins.

  DOI：

  10.1021/jo011185a

文献信息

• Hybrid phosphoinositide phospholipids: compositions and uses
  申请人：Prestwich Glenn

  公开号：US20050148042A1

  公开（公告）日：2005-07-07

  The methods and compositions disclosed herein concern the synthesis of a novel class of “two-headed” phospholipid-phosphoinositide hybrids possessing a carbon backbone, such as 2,3-diacylthreitol, erythritol or a synthetic module. The second phospholipid head group allows introduction of a biochemical or chemical moiety in a position orthogonal in space to those occupied by the phosphoinositide head group and the two acyl chains. The diacyl moieties allow for the incorporation of Pea-PIP 2 into a lipid bilayer, while the Ptdlns(4,5)P 2 moiety in the aqueous layer is specifically recognized by lipid binding proteins. In alternative embodiments of the invention, reporters, for example biotin, fluorophores and/or spin labels, are attached to the free amino group of the head groups of such molecules to specifically target the reporters to the lipid-water interface.

  本文所披露的方法和组合物涉及合成一种新型的“双头”磷脂酰肌醇酰杂交物，具有碳骨架，例如2,3-二酰基己二醇、赤藓糖或合成模块。第二个磷脂酰头基允许在空间上与磷脂酰肌醇头基和两个酰基链所占据的位置相垂直引入生化或化学基团。二酰基基团允许将豌豆-PIP2并入脂质双层，而水相层中的Ptdlns（4,5）P2基团则被脂质结合蛋白特异性识别。在发明的其他实施方式中，例如生物素、荧光染料和/或自旋标记，附加在此类分子头基的自由氨基上，以特异性地将报告物靶向到脂质-水界面。