N⁶-cyanomethyl-2',3',5'-tri-O-acetyladenosine

• 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: N⁶-cyanomethyl-2',3',5'-tri-O-acetyladenosine
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-(cyanomethylamino)purin-9-yl]oxolan-2-yl]methyl acetate
• 化学式: C₁₈H₂₀N₆O₇
• 分子量: 432.393
• InChiKey: QLOKRNJKLNLWIP-SCFUHWHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  168
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  2',3',5'-三乙酰腺苷 在 1,3,6,8-tetra-n-butylpyrimido<5,4-g>pteridine-2,4,5,7(1H,3H,6H,8H)-tetrone 10-oxide 作用下， 以 正丁醇 为溶剂， 反应 0.83h， 生成 N⁶-cyanomethyl-2',3',5'-tri-O-acetyladenosine
  参考文献：
  名称：

  Distinct Solvent-Dependence in the Photoreactions of Purine Nucleosides with Pyrimido[5,4-g]pteridinetetrone N-Oxide: Possible Generatiion of Hydroxyl Radical from the Excited N-Oxide in Alcohols

  摘要：

  Photoreaction of 2',3',5'-tri-O-acetyladenosine (5) with pyrimido[5,4-g]pteridinetetrone N-oxide (1) in acetonitrile gave N6-cyanomethyl-2',3',5'-tri-O-acetyladenosine (6) as a major detectable product via coupling of adenosyl radical with cyanomethyl radical generated by the mediation of 1. Under the analogous conditions, N2-benzoyl-2',3',5'-tri-O-acetylguanosine (8) underwent oxidative degradation of the guanine skeleton by 1. In sharp contrast, photoreactions of 5 and 8 with 1 in tert-butanol resulted in the formation of the corresponding 8-hydroxypurine nucleosides (7) and (9), respectively. These facts and other observations suggest that 1 could generate hydroxyl radical upon irradiation in alcohols.

  DOI：

  10.3987/com-92-s20

文献信息

• Distinct Solvent-Dependence in the Photoreactions of Purine Nucleosides with Pyrimido[5,4-g]pteridinetetrone N-Oxide: Possible Generatiion of Hydroxyl Radical from the Excited N-Oxide in Alcohols
  作者：Yoshifumi Maki、Toru Makino、Kosaku Hirota、Magoichi Sako

  DOI：10.3987/com-92-s20

  日期：——

  Photoreaction of 2',3',5'-tri-O-acetyladenosine (5) with pyrimido[5,4-g]pteridinetetrone N-oxide (1) in acetonitrile gave N6-cyanomethyl-2',3',5'-tri-O-acetyladenosine (6) as a major detectable product via coupling of adenosyl radical with cyanomethyl radical generated by the mediation of 1. Under the analogous conditions, N2-benzoyl-2',3',5'-tri-O-acetylguanosine (8) underwent oxidative degradation of the guanine skeleton by 1. In sharp contrast, photoreactions of 5 and 8 with 1 in tert-butanol resulted in the formation of the corresponding 8-hydroxypurine nucleosides (7) and (9), respectively. These facts and other observations suggest that 1 could generate hydroxyl radical upon irradiation in alcohols.