9-[(2R,3S,4S,5R)-3-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-4-[(5-nitropyridin-2-yl)disulfanyl]oxolan-2-yl]-1H-purin-6-one | 174467-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 9-[(2R,3S,4S,5R)-3-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-4-[(5-nitropyridin-2-yl)disulfanyl]oxolan-2-yl]-1H-purin-6-one
• CAS: 174467-01-7
• 化学式: C₃₅H₃₀N₆O₇S₂
• 分子量: 710.791
• InChiKey: CYCGQLLNTFGPQS-CIBJAQMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  217
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  9-[(2R,3S,4S,5R)-3-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-4-[(5-nitropyridin-2-yl)disulfanyl]oxolan-2-yl]-1H-purin-6-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and Characterization of an RNA Dinucleotide Containing a 3‘-S-Phosphorothiolate Linkage

  摘要：

  The synthesis of an RNA dinucleotide (IspU) containing a 3'-S-phosphorothiolate linkage is described. The compound is prepared from 9-(3-deoxy-3-iodo-beta-D-xylofuranosyl)hyperanthine with installation of the phosphorothiolate group via an Arbusov reaction and protection of the ribose 2'-hydroxyl as a silyl ether. IspU is found to be a substrate for several enzymes including T4 polynucleotide kinase, snake venom phosphodiesterase, and ribonuclease T-2. Base-catalyzed cleavage of the dinucleotide is accelerated (similar to 2000-fold) relative to that of the phosphate-linked compound IpU. Product characterization and kinetic analysis show that IspU is cleaved through the same mechanism as IpU. The observed rate acceleration is argued to reflect stabilization of the anionic transition state by the polarizable sulfur atom.

  DOI：

  10.1021/ja9616903
• 作为产物：
  描述：

  9-(3-deoxy-3-iodo-β-D-xylofuranosyl)hypoxanthine 在 吡啶 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.5h， 生成 9-[(2R,3S,4S,5R)-3-hydroxy-5-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]-4-[(5-nitropyridin-2-yl)disulfanyl]oxolan-2-yl]-1H-purin-6-one
  参考文献：
  名称：

  Synthesis and Characterization of an RNA Dinucleotide Containing a 3‘-S-Phosphorothiolate Linkage

  摘要：

  The synthesis of an RNA dinucleotide (IspU) containing a 3'-S-phosphorothiolate linkage is described. The compound is prepared from 9-(3-deoxy-3-iodo-beta-D-xylofuranosyl)hyperanthine with installation of the phosphorothiolate group via an Arbusov reaction and protection of the ribose 2'-hydroxyl as a silyl ether. IspU is found to be a substrate for several enzymes including T4 polynucleotide kinase, snake venom phosphodiesterase, and ribonuclease T-2. Base-catalyzed cleavage of the dinucleotide is accelerated (similar to 2000-fold) relative to that of the phosphate-linked compound IpU. Product characterization and kinetic analysis show that IspU is cleaved through the same mechanism as IpU. The observed rate acceleration is argued to reflect stabilization of the anionic transition state by the polarizable sulfur atom.

  DOI：

  10.1021/ja9616903

文献信息

• Preparation, Hydrolysis and Intramolecular Transesterification of 3′-Deoxy-3′-thioinosine 3′-S-Dimethylphosphorothiolate
  作者：Mohamed I. Elzagheid、Esa Mäki、Ulla Kaukinen、Mikko Oivanen、Harri Lönnberg

  DOI：10.1080/15257770008035028

  日期：2000.4

  The hydrolytic reactions of the dimethyl ester of 3'-deoxy-3'-thioinosine 3'-S-phosphorothiolate have been followed over a wide aciditiy range by HPLC. At pH > 3, only hydroxide ion catalyzed isomerization to the 2'-dimethylphosphate takes place, whereas under more acidic conditions hydrolysis to the 2'-monomethylphosphate and 3'-S-monomethylphosphorothiolate competes. The latter is the only product accumulating in very acidic solutions (1 M hydrochloric acid). Mechanisms of the reactions are discussed.
• Synthesis and Characterization of an RNA Dinucleotide Containing a 3‘-<i>S</i>-Phosphorothiolate Linkage
  作者：Lara B. Weinstein、David J. Earnshaw、Richard Cosstick、Thomas R. Cech

  DOI：10.1021/ja9616903

  日期：1996.1.1

  The synthesis of an RNA dinucleotide (IspU) containing a 3'-S-phosphorothiolate linkage is described. The compound is prepared from 9-(3-deoxy-3-iodo-beta-D-xylofuranosyl)hyperanthine with installation of the phosphorothiolate group via an Arbusov reaction and protection of the ribose 2'-hydroxyl as a silyl ether. IspU is found to be a substrate for several enzymes including T4 polynucleotide kinase, snake venom phosphodiesterase, and ribonuclease T-2. Base-catalyzed cleavage of the dinucleotide is accelerated (similar to 2000-fold) relative to that of the phosphate-linked compound IpU. Product characterization and kinetic analysis show that IspU is cleaved through the same mechanism as IpU. The observed rate acceleration is argued to reflect stabilization of the anionic transition state by the polarizable sulfur atom.