9-(3-deoxy-3-iodo-β-D-xylofuranosyl)hypoxanthine | 54883-90-8

• 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: 9-(3-deoxy-3-iodo-β-D-xylofuranosyl)hypoxanthine
• 英文别名: 9-(3-iodo-β-D-3-deoxy-xylofuranosyl)-1,9-dihydro-purin-6-one
• CAS: 54883-90-8
• 化学式: C₁₀H₁₁IN₄O₄
• 分子量: 378.126
• InChiKey: UUESTCZDMWAUTH-GQTRHBFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.83
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113.26
• 氢给体数：
  3.0
• 氢受体数：
  7.0

文献信息

• Allylic Substitution of 3‘,4‘-Unsaturated Nucleosides:  Organosilicon-Based Stereoselective Access to 4‘-<i>C</i>-Branched 2‘,3‘-Didehydro-2‘,3‘-dideoxyribonucleosides
  作者：Kazuhiro Haraguchi、Hiromichi Tanaka、Yoshiharu Itoh、Kentaro Yamaguchi、Tadashi Miyasaka

  DOI：10.1021/jo9516190

  日期：1996.1.1

  Reactions of organosilicon reagents (such as allyltrimethylsilane, silyl enol ethers, cyanotrimethylsilane) with 3',4'-unsaturated nucleosides (of uracil, N-4-acetylcytosine, and hypoxanthine) having an allyl ester structure were investigated in the presence of a Lewis acid in CH2Cl2. In the cases of uracil and N-4-acetylcytosine derivatives, SnCl4 appeared to be suitable, whereas the use of EtAlCl(2) was necessary for the hypoxanthine derivatives. The main pathway of these reactions was found to be a-face-selective S(N)2' allylic substitution, irrespective of the configuration of 2'-0-acyl leaving group. As a result, a new stereoselective operation for C-C bonds formation leading to 4'-carbon-substituted 2',3'-didehydro-2',3'-dideoxyribonucleosides has been disclosed for the first time. Stereochemistry of these 4'-C-branched products can be assigned on the basis of H-1 NMR spectroscopy in terms of the anisotropic shift of H-5 of the pyrimidine base (or H-8 of the hypoxanthine), which is caused by the 5'-0-(tert-butyldiphenylsilyl) protecting group.
• 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.