Phosphoric acid mono-[(3aR,4R,6R,6aR)-6-(6-amino-8-bromo-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester | 176747-05-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: Phosphoric acid mono-[(3aR,4R,6R,6aR)-6-(6-amino-8-bromo-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester
• CAS: 176747-05-0
• 化学式: C₁₃H₁₇BrN₅O₇P
• 分子量: 466.185
• InChiKey: DTYKZLYFPIJTHN-IOSLPCCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  164.07
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  Phosphoric acid mono-[(3aR,4R,6R,6aR)-6-(6-amino-8-bromo-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester 在 六甲基磷酰三胺 、 三辛胺 、 硫酸 、 三乙胺 、 氯磷酸二苯酯 作用下， 以 1,4-二氧六环 、 甲醇 、 氯仿 、 水 为溶剂， 反应 4.5h， 生成 C8-{[(dioctadecyl)amino]succinylaminohexylamino}adenosine-5'-(β,γ-methylene-triphosphate)
  参考文献：
  名称：

  ATP-LipidsProtein Anchor and Energy Source in Two Dimensions

  摘要：

  The ubiquitous function of ATP as energy equivalent in nature has resulted in a common folding pattern of ATP-binding proteins. Their binding pocket tolerates modifications of the adenine ring to some extend, whereas those of the triphosphate group strongly affect the binding affinity. In consequence, immobilized C8- and N-6- modified ATP analogues are frequently used for affinity purification of ATPases or kinases. To combine this unique recognition principle with the fascinating properties of self-assembly, we have synthesized a novel class of hydrolyzable and nonhydrolyzable ATP-lipids where the nucleotides are covalently attached via C8- or N-6-position of the adenine ring to a synthetic lipid. These ATP-lipids were characterized by various enzyme assays in micellar solution, resulting in ATPase and competition activities that are comparable to their free counterparts. The specific docking of actin as a model of an ATP-binding protein to ATP-lipid monolayers was followed by film balance technique and epifluorescence microscopy. Based on this specific interaction, actin-supported membranes were generated to study shape transitions of vesicular systems. Due to the coupling of actin to ATP-lipid bilayers drastic changes in the viscoelastic properties and shape transitions were observed by phase contrast microscopy. These results underline the properties of these novel ATP-lipids as protein anchor or energy source in two dimensions. They can be applied either to form phantom cells, actin-supported membranes or to orient and crystallize ATP-binding proteins at lipid interfaces.

  DOI：

  10.1021/ja953937m
• 作为产物：
  描述：

  在 lead(IV) acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以90%的产率得到Phosphoric acid mono-[(3aR,4R,6R,6aR)-6-(6-amino-8-bromo-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl] ester
  参考文献：
  名称：

  ATP-LipidsProtein Anchor and Energy Source in Two Dimensions

  摘要：

  The ubiquitous function of ATP as energy equivalent in nature has resulted in a common folding pattern of ATP-binding proteins. Their binding pocket tolerates modifications of the adenine ring to some extend, whereas those of the triphosphate group strongly affect the binding affinity. In consequence, immobilized C8- and N-6- modified ATP analogues are frequently used for affinity purification of ATPases or kinases. To combine this unique recognition principle with the fascinating properties of self-assembly, we have synthesized a novel class of hydrolyzable and nonhydrolyzable ATP-lipids where the nucleotides are covalently attached via C8- or N-6-position of the adenine ring to a synthetic lipid. These ATP-lipids were characterized by various enzyme assays in micellar solution, resulting in ATPase and competition activities that are comparable to their free counterparts. The specific docking of actin as a model of an ATP-binding protein to ATP-lipid monolayers was followed by film balance technique and epifluorescence microscopy. Based on this specific interaction, actin-supported membranes were generated to study shape transitions of vesicular systems. Due to the coupling of actin to ATP-lipid bilayers drastic changes in the viscoelastic properties and shape transitions were observed by phase contrast microscopy. These results underline the properties of these novel ATP-lipids as protein anchor or energy source in two dimensions. They can be applied either to form phantom cells, actin-supported membranes or to orient and crystallize ATP-binding proteins at lipid interfaces.

  DOI：

  10.1021/ja953937m