5'-O-phosphoryl-2'-deoxyadenylyl-(3'->5')-1',3'-dideoxy-2'-isoadenosine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: 5'-O-phosphoryl-2'-deoxyadenylyl-(3'->5')-1',3'-dideoxy-2'-isoadenosine
• 英文别名: [(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(phosphonooxymethyl)tetrahydrofuran-3-yl] [(2S,4S)-4-(6-aminopurin-9-yl)tetrahydrofuran-2-yl]methyl hydrogen phosphate；[(2S,4S)-4-(6-aminopurin-9-yl)oxolan-2-yl]methyl [(2R,3S,5R)-5-(6-aminopurin-9-yl)-2-(phosphonooxymethyl)oxolan-3-yl] hydrogen phosphate
• 化学式: C₂₀H₂₆N₁₀O₁₀P₂
• 分子量: 628.435
• InChiKey: CBSKDKCHKOJBHK-QSLWVIQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  280
• 氢给体数：
  5
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  6-N-benzoyl-P-(2-cyanoethyl)-2'-deoxyadenylyl-(3'->5')-6-N-benzoyl-1',3'-dideoxy-2'-isoadenosine 在 吡啶 、 四氮唑 、 ammonium hydroxide 、 水 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 5'-O-phosphoryl-2'-deoxyadenylyl-(3'->5')-1',3'-dideoxy-2'-isoadenosine
  参考文献：
  名称：

  Inhibition of the strand transfer step of HIV-1 integrase by non-natural dinucleotides

  摘要：

  New, non-natural dinucleotide 5'-monophosphates, with a surrogate isonucleoside component Of L-related stereochemistry at the 'terminal' position, have been synthesized. Structures of 2a-c were confirmed by multinuclear NMR spectra (H-1, C-13, (31)p, COSY), UV hypochromicity and FAB HRMS data. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. The dinucleotides showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of selective strand transfer inhibitors of HIV integrase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.050

文献信息

• Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest
  作者：Guochen Chi、Vasu Nair

  DOI：10.1080/15257770500265703

  日期：2005.9.1

  New, nonnatural dinucleotide 5'-monophosphates with a surrogate isonucleoside component of L-related stereochemistry, have been synthesized. Structures of the target compounds were confirmed by multinuclear NMR spectra (H-1, C-13, P-31, COSY), UV hypochromicity, FAB HRMS data and X-ray crystallography. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. Dinucleotides of this study with a terminal L-isonucleoside component showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of this type of selectivity of inhibition of the strand transfer step.
• Inhibition of the strand transfer step of HIV-1 integrase by non-natural dinucleotides
  作者：Guochen Chi、Nouri Neamati、Vasu Nair

  DOI：10.1016/j.bmcl.2004.07.050

  日期：2004.10

  New, non-natural dinucleotide 5'-monophosphates, with a surrogate isonucleoside component Of L-related stereochemistry at the 'terminal' position, have been synthesized. Structures of 2a-c were confirmed by multinuclear NMR spectra (H-1, C-13, (31)p, COSY), UV hypochromicity and FAB HRMS data. These compounds are totally resistant to cleavage by 3'- and 5'-exonucleases. The dinucleotides showed remarkable selectivity for inhibition of the strand transfer step of HIV-1 integrase. To the best of our knowledge, these compounds represent only the second example of selective strand transfer inhibitors of HIV integrase. (C) 2004 Elsevier Ltd. All rights reserved.