(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(((hydroxy((hydroxy(phosphonooxy)phosphoryl)oxy)phosphoryl)oxy)methyl)tetrahydrofuran-3-yl 4-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)benzoate | 1313806-65-3

• 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: (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(((hydroxy((hydroxy(phosphonooxy)phosphoryl)oxy)phosphoryl)oxy)methyl)tetrahydrofuran-3-yl 4-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)benzoate
• CAS: 1313806-65-3
• 化学式: C₂₇H₃₅N₈O₁₆P₃S
• 分子量: 852.606
• InChiKey: NZQQLUZADTXJNX-LDAIXZEYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  55.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  355.43
• 氢给体数：
  9.0
• 氢受体数：
  18.0

反应信息

• 作为产物：
  描述：

  N-(+)-生物素基-4-氨基苯甲酸 、 5’-三磷酸腺苷 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 7.0h， 生成 (2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-hydroxy-5-(((hydroxy((hydroxy(phosphonooxy)phosphoryl)oxy)phosphoryl)oxy)methyl)tetrahydrofuran-3-yl 4-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)benzoate 、 (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(((hydroxy((hydroxy(phosphonooxy)phosphoryl)oxy)phosphoryl)oxy)methyl)tetrahydrofuran-3-yl 4-(5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamido)benzoate
  参考文献：
  名称：

  Design and Synthesis of ATP-Based Nucleotide Analogues and Profiling of Nucleotide-Binding Proteins

  摘要：

  Two nucleotide-based probes were designed and synthesized in order to enrich samples for specific classes of proteins by affinity-based protein profiling. We focused on the profiling of adenine nucleotide-binding proteins. Two properties were considered in the design of the probes: the bait needs to bind adenine nucleotide-binding proteins with high affinity and carry a second functional group suitable and easily accessible for coupling to a chromatography resin. For this purpose, we synthesized p-biotinyl amidobenzoic acid-ATP (p-BABA-ATP) and p-biotinyl aminomethylbenzoic acid-ATP (p-BAMBA-ATP). p-BABA-ATP and p-BAMBA-ATP both bind to ATP-binding cassette (ABC) proteins with at least 10-fold higher affinity than ATP. Several ABC transporters could be enriched using p-BABA-ATP or p-BAMBA-ATP.

  DOI：

  10.1021/bc100592q