(S)-5-{[(3aR,4R,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-methoxy-phosphoryloxy}-4-benzyloxycarbonylamino-pentanoic acid benzyl ester | 212714-85-7

• 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: (S)-5-{[(3aR,4R,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-methoxy-phosphoryloxy}-4-benzyloxycarbonylamino-pentanoic acid benzyl ester
• CAS: 212714-85-7
• 化学式: C₄₁H₄₅N₆O₁₂P
• 分子量: 844.815
• InChiKey: NXBNQKZCGKMSNO-YMDWVCNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  60.0
• 可旋转键数：
  18.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  209.78
• 氢给体数：
  2.0
• 氢受体数：
  16.0

反应信息

• 作为反应物：
  描述：

  (S)-5-{[(3aR,4R,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-methoxy-phosphoryloxy}-4-benzyloxycarbonylamino-pentanoic acid benzyl ester 在 三氟乙酸 作用下， 反应 0.17h， 以93%的产率得到(S)-5-{[(2R,3S,4R,5R)-5-(6-Benzoylamino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-methoxy-phosphoryloxy}-4-benzyloxycarbonylamino-pentanoic acid benzyl ester
  参考文献：
  名称：

  Glutamyl Adenylate Analogues Are Inhibitors of Glutamyl-tRNA Synthetase

  摘要：

  Glutamol adenylate 10 was a competitive inhibitor (K-i = 3 pM) of glutamyl-tRNA synthetase from Escherichia coli. The N-6-benzoyl adenine derivative 9 was also an inhibitor (K-i similar to 60 mu M). Replacement of adenine by other bases (purine, cytosine, dihydrocytosine, uridine) resulted in a more than 1000-fold loss in activity, indicating the important contribution of the adenine ring to the enzyme binding. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1082
• 作为产物：
  描述：

  在 四氮唑 、 碘 作用下， 以 四氢呋喃 、 吡啶 、 乙腈 为溶剂， 反应 5.0h， 生成 (S)-5-{[(3aR,4R,6R,6aR)-6-(6-Benzoylamino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy]-methoxy-phosphoryloxy}-4-benzyloxycarbonylamino-pentanoic acid benzyl ester
  参考文献：
  名称：

  Glutamyl Adenylate Analogues Are Inhibitors of Glutamyl-tRNA Synthetase

  摘要：

  Glutamol adenylate 10 was a competitive inhibitor (K-i = 3 pM) of glutamyl-tRNA synthetase from Escherichia coli. The N-6-benzoyl adenine derivative 9 was also an inhibitor (K-i similar to 60 mu M). Replacement of adenine by other bases (purine, cytosine, dihydrocytosine, uridine) resulted in a more than 1000-fold loss in activity, indicating the important contribution of the adenine ring to the enzyme binding. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1082