N-[2-[[4-[4-(4-aminophenyl)buta-1,3-dienyl]phenyl]ethylamino]ethyl]-1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranuronamide | 937018-49-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N-[2-[[4-[4-(4-aminophenyl)buta-1,3-dienyl]phenyl]ethylamino]ethyl]-1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranuronamide
• CAS: 937018-49-0
• 化学式: C₃₀H₃₄N₈O₄
• 分子量: 570.651
• InChiKey: TVHOLDKYOGCOSS-LBJNWJBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  177.67
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  N-[2-[[4-[4-(4-aminophenyl)buta-1,3-dienyl]phenyl]ethylamino]ethyl]-1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranuronamide 在 四氮唑 、 氧气 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synchronous Photoinitiation of Endothelial NO Synthase Activity by a Nanotrigger Targeted at Its NADPH Site

  摘要：

  We designed a new nanotrigger to synchronize and monitor an enzymatic activity interacting specifically with the conserved NADPH binding site. The nanotrigger (NT) combines a docking moiety targeting the NADPH site and a chromophore moiety responsive to light excitation for efficient electron transfer to the protein. Specific binding of the nanotrigger to the reductase domain of the endothelial nitric oxide synthase (eNOSred) was demonstrated by competition between NADPH and the nanotrigger on the reduction of eNOSred flavin. A micromolar K-i was estimated. We had monitored initiation of eNOSred activity by ultrafast transient spectroscopy. The transient absorption spectrum recorded at 250 ps fits the expected sum of the reduced and oxidized species, independently obtained by other chemical methods, in agreement with a photoinduced electron transfer from the excited nanotrigger to the flavin moiety of eNOSred. The rate of electron transfer from the excited state of the nanotrigger (NT*) to the protein is estimated to be k(ET) = (7 +/- 2) x 10(9) s(-1) using the decay of oxidized eNOSred-bound nanotrigger compared against prereduced eNOSred or glucose 6-P dehydrogenase as controls. This fast electron transfer bypasses the slow hydride transfer to initiate NOS catalysis as shown by ultrafast kinetics using the eNOSred mutated in the regulatory F1160 residue. The selective targeting of the nanotrigger to NADPH sites should allow controlled initiation of the enzymatic activity of numerous proteins containing an NADPH site.

  DOI：

  10.1021/ja067543e
• 作为产物：
  描述：

  4-{N-ethyl-N-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl] amino}benzaldehyde 在 吡啶 、 盐酸 、 sodium hydroxide 、 sodium azide 、 sodium hydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 234.0h， 生成 N-[2-[[4-[4-(4-aminophenyl)buta-1,3-dienyl]phenyl]ethylamino]ethyl]-1-(6-amino-9H-purin-9-yl)-1-deoxy-β-D-ribofuranuronamide
  参考文献：
  名称：

  NADPH替代品通过双光子诱导的电子转移选择性还原反应过程的光引发。

  摘要：

  将NADPH替代物（其中烟酰胺部分被发色单位所取代，该发色单位具有更大的双光子吸收截面，并且仅在激发时才能够将电子转移到黄素上）描述为有效的双光子纳米触发，用于电子转移的选择性光活化在生物还原过程中。

  DOI：

  10.1039/b615628b