adenosine-5'-carboxylic acid butyl ester | 35927-11-8

• 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: adenosine-5'-carboxylic acid butyl ester
• 英文别名: 1-(6-amino-purin-9-yl)-β-D-1-deoxy-ribofuranuronic acid butyl ester；Adenosin-5'-carbonsaeure-n-butylester；n-butyladenosin-5'-carboxylat；butyl (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolane-2-carboxylate
• CAS: 35927-11-8
• 化学式: C₁₄H₁₉N₅O₅
• 分子量: 337.335
• InChiKey: QYWOCBLQFXTDKN-MPXOCVNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  腺苷酸-5-羧酸 、 正丁醇 在 氯化亚砜 作用下， 反应 60.0h， 以13%的产率得到adenosine-5'-carboxylic acid butyl ester
  参考文献：
  名称：

  Inactivation of S-Adenosyl-l-homocysteine Hydrolase by Amide and Ester Derivatives of Adenosine-5‘-carboxylic Acid

  摘要：

  S-Adenosyl-L-homocysteine (AdoHcy) hydrolase has been shown to have (5'/6') hydrolytic activity with vinyl (5') or homovinyl (6') halides derived from adenosine (Ado). This hydrolytic activity is independent of its 3'-oxidative activity. The vinyl (or homovinyl) halides are converted into 5'(or 6')-carboxaldehydes by the hydrolytic activity of the enzyme, and inactivation occurs via the oxidative activity. Amide and ester derivatives of Ado-5'-carboxylic acid were prepared to further probe the hydrolytic capability of AdoHcy hydrolase. The oxidative activity (but not the hydrolytic activity) is involved in the mechanism of inhibition of the enzyme by the ester and amide derivatives of Ado-5'-carboxylic acid, in contrast to the inactivation of this enzyme by adenosine-derived vinyl or homovinyl halide analogues during which both activities are manifested.

  DOI：

  10.1021/jm960313y

文献信息

• Inactivation of <i>S-</i>Adenosyl-<scp>l</scp>-homocysteine Hydrolase by Amide and Ester Derivatives of Adenosine-5‘-carboxylic Acid
  作者：Stanislaw F. Wnuk、Siming Liu、Chong-Sheng Yuan、Ronald T. Borchardt、Morris J. Robins

  DOI：10.1021/jm960313y

  日期：1996.1.1

  S-Adenosyl-L-homocysteine (AdoHcy) hydrolase has been shown to have (5'/6') hydrolytic activity with vinyl (5') or homovinyl (6') halides derived from adenosine (Ado). This hydrolytic activity is independent of its 3'-oxidative activity. The vinyl (or homovinyl) halides are converted into 5'(or 6')-carboxaldehydes by the hydrolytic activity of the enzyme, and inactivation occurs via the oxidative activity. Amide and ester derivatives of Ado-5'-carboxylic acid were prepared to further probe the hydrolytic capability of AdoHcy hydrolase. The oxidative activity (but not the hydrolytic activity) is involved in the mechanism of inhibition of the enzyme by the ester and amide derivatives of Ado-5'-carboxylic acid, in contrast to the inactivation of this enzyme by adenosine-derived vinyl or homovinyl halide analogues during which both activities are manifested.