5'-O-acetylinosine | 28526-32-1

• 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: 5'-O-acetylinosine
• 英文别名: Inosine, 5'-acetate；[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 28526-32-1
• 化学式: C₁₂H₁₄N₄O₆
• 分子量: 310.266
• InChiKey: FZGRVVNNENJDMC-WOUKDFQISA-N

物化性质

• 熔点：
  228-230 °C(Solv: methanol (67-56-1))
• 沸点：
  728.3±60.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5'-O-acetyladenosine 在 adenylate deaminase 、 二甲基亚砜 作用下， 以 phosphate buffer 为溶剂， 反应 0.17h， 以97%的产率得到5'-O-acetylinosine
  参考文献：
  名称：

  腺苷酸脱氨酶（5'-腺苷酸脱氨酶，AMPDA）-催化 5'-脱氧-5'-取代和 5'-保护的腺苷脱氨：与腺苷脱氨酶 (ADA) 催化活性的比较

  摘要：

  腺苷酸脱氨酶 (AMPDA) 能够催化 5'-取代和 5'-保护的 5'-脱氧腺苷的水解脱氨，而腺苷脱氨酶 (ADA) 对相同底物的活性有限或没有活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  DOI：

  10.1002/ejoc.200300435

文献信息

• Clay‐Mediated Selective Hydrolysis of 5′‐<i>O</i>‐Acetyl‐2′,3′‐isopropylidene/Cyclohexylidene Nucleosides
  作者：Mukund K. Gurjar、Dhananjoy Mondal、S. V. Ravindranadh、Mukund S. Chorghade

  DOI：10.1080/00397910600639968

  日期：2006.8

  Abstract A generalized procedure for the selective hydrolysis of 5′‐O‐acetyl‐2′,3′‐isopropylidene/cyclohexylidene nucleosides with a solid catalyst, Montmorillonite K‐10 in refluxing methanol, to furnish 5′‐O‐acetyl‐nucleosides is described.

  摘要 用固体催化剂蒙脱石 K-10 在回流甲醇中选择性水解 5'-O-乙酰基-2',3'-异亚丙基/亚环己基核苷以提供 5'-O-乙酰基核苷的通用程序是描述。
• Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium
  作者：Lidiane Meier、Gustavo C. Monteiro、Rodrigo A. M. Baldissera、Marcus Mandolesi Sá

  DOI：10.1590/s0103-50532010000500013

  日期：——

  A straightforward methodology for deacetylation of protected ribonucleosides was developed based on triethylamine-catalyzed solvolysis in aqueous methanol. Reactions are completed in a few minutes under microwave irradiation and the free nucleosides are obtained in high yield after simple evaporation of volatiles. Other important features include the involvement of readily available reagents and the compatibility with diverse functional groups, which make this process very attractive for broad application.
• Ishido, Yoshiharu; Sakairi, Nobuo; Okazaki, Kei, Journal of the Chemical Society. Perkin transactions I, 1980, p. 563 - 573
  作者：Ishido, Yoshiharu、Sakairi, Nobuo、Okazaki, Kei、Nakazaki, Nobuo

  DOI：——

  日期：——
• Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine: A new chemoenzymatic synthesis of the antiviral drug 2′,3′-dideoxyinosine
  作者：Pierangela Ciuffreda、Silvana Casati、Enzo Santaniello

  DOI：10.1016/s0960-894x(99)00228-0

  日期：1999.6

  The selective acylation of the hydroxy groups of the nucleosides inosine la and 2'-deoxyinosine Ib has been achieved in the presence of Candida antarctica and Pseudomonas sp. lipases in organic solvents; starting from the 5'-acetyl derivative of 2'-deoxyinosine, compound 5a, an efficient chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine 1c has been achieved, (C) 1999 Elsevier Science Ltd. All rights reserved.
• Adenylate Deaminase (5′-Adenylic Acid Deaminase, AMPDA)-Catalyzed Deamination of 5′-Deoxy-5′-Substituted and 5′-Protected Adenosines: A Comparison with the Catalytic Activity of Adenosine Deaminase (ADA)
  作者：Pierangela Ciuffreda、Angela Loseto、Laura Alessandrini、Giancarlo Terraneo、Enzo Santaniello

  DOI：10.1002/ejoc.200300435

  日期：2003.12

  The enzyme adenylate deaminase (AMPDA) is able to catalyze the hydrolytic deamination of 5′-substituted and 5′-protected 5′-deoxyadenosines, whereas limited or no activity is shown by adenosine deaminase (ADA) towards the same substrates. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  腺苷酸脱氨酶 (AMPDA) 能够催化 5'-取代和 5'-保护的 5'-脱氧腺苷的水解脱氨，而腺苷脱氨酶 (ADA) 对相同底物的活性有限或没有活性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)