N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine | 619671-54-4

• 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: N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine
• 英文别名: n1-(2-Carboxy-2-hydroxyethyl)deoxyadenosine；2-hydroxy-3-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-iminopurin-1-yl]propanoic acid
• CAS: 619671-54-4
• 化学式: C₁₃H₁₇N₅O₆
• 分子量: 339.308
• InChiKey: VCNAQVOCEVGTKU-KKVHJZIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  165
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine 以 phosphate buffer 为溶剂， 反应 24.0h， 生成 N⁶-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine
  参考文献：
  名称：

  Reaction of Glycidamide with 2′-Deoxyadenosine and 2′-Deoxyguanosine—Mechanism for the Amide Hydrolysis

  摘要：

  2'-Deoxyadenosine (dA) and 2'-deoxyguanosine (dG) were reacted with the mutagenic epoxide glycidamide (GA, Scheme 1). The reactions yielded three GA-dA adducts (NI-GA-dA, N-6-GA-dA and N1-GA-dI) and two GA-dG adducts (N1-GA-dG I and N1-GA-dG II) (Scheme 2). The structures of the adducts were characterized by spectroscopic and spectrometric methods (H-1-C-13, and 2D NMR, MS, UV). The mechanism of the amide hydrolysis taking place during formation of the adducts N1-GA-dA and N1-GA-dG I was studied. We propose a mechanism where a transamidation is the key step in the hydrolysis of the amide function of GA.

  DOI：

  10.1080/15257770601112697
• 作为产物：
  描述：

  在 水 作用下， 生成 N1-(2-carboxy-2-hydroxyethyl)-2'-deoxyadenosine 、 2'-脱氧腺苷
  参考文献：
  名称：

  Reaction of Glycidamide with 2′-Deoxyadenosine and 2′-Deoxyguanosine—Mechanism for the Amide Hydrolysis

  摘要：

  2'-Deoxyadenosine (dA) and 2'-deoxyguanosine (dG) were reacted with the mutagenic epoxide glycidamide (GA, Scheme 1). The reactions yielded three GA-dA adducts (NI-GA-dA, N-6-GA-dA and N1-GA-dI) and two GA-dG adducts (N1-GA-dG I and N1-GA-dG II) (Scheme 2). The structures of the adducts were characterized by spectroscopic and spectrometric methods (H-1-C-13, and 2D NMR, MS, UV). The mechanism of the amide hydrolysis taking place during formation of the adducts N1-GA-dA and N1-GA-dG I was studied. We propose a mechanism where a transamidation is the key step in the hydrolysis of the amide function of GA.

  DOI：

  10.1080/15257770601112697