6-Chlor-(2',3'-O-isopropyliden-9-ss-D-ribofuranosyl)purin-5'-phosphat | 39824-27-6

• 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: 6-Chlor-(2',3'-O-isopropyliden-9-ss-D-ribofuranosyl)purin-5'-phosphat
• 英文别名: 1-(6-chloro-purin-9-yl)-O²,O³-isopropylidene-O⁵-phosphono-β-D-1-deoxy-ribofuranose；6-Chloro-9-[2,3-O-(1-methylethylidene)-5-O-phosphono-I(2)-D-ribofuranosyl]-9H-purine；[(3aR,4R,6R,6aR)-4-(6-chloropurin-9-yl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methyl dihydrogen phosphate
• CAS: 39824-27-6
• 化学式: C₁₃H₁₆ClN₄O₇P
• 分子量: 406.719
• InChiKey: RGJAJLKDYCLAAE-WOUKDFQISA-N

物化性质

• 沸点：
  648.5±65.0 °C(Predicted)
• 密度：
  1.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.01
• 重原子数：
  26.0
• 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：
  138.05
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  6-Chlor-(2',3'-O-isopropyliden-9-ss-D-ribofuranosyl)purin-5'-phosphat 在 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 Phosphoric acid mono-((3aR,4R,6R,6aR)-6-{6-[2-(3-dioctadecylcarbamoyl-propionylamino)-ethylamino]-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
• 作为产物：
  描述：

  6-氯-9-beta-D-(2,3-异亚丙基)呋喃核糖基嘌呤 在 2,6-二甲基吡啶 、 lead(IV) acetate 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 6-Chlor-(2',3'-O-isopropyliden-9-ss-D-ribofuranosyl)purin-5'-phosphat
  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