5'-O-phosphoryl-1'-deoxy-2'-isoadenylyl-(3'->5')-uridine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 5'-O-phosphoryl-1'-deoxy-2'-isoadenylyl-(3'->5')-uridine
• 英文别名: [(2R,3S,4R)-4-(6-aminopurin-9-yl)-2-(phosphonooxymethyl)tetrahydrofuran-3-yl] [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl hydrogen phosphate；[(2R,3S,4R)-4-(6-aminopurin-9-yl)-2-(phosphonooxymethyl)oxolan-3-yl] [(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• 化学式: C₁₉H₂₅N₇O₁₄P₂
• 分子量: 637.394
• InChiKey: IKRRYXCUXRSDDG-AONHZOMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  42
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  301
• 氢给体数：
  7
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  N³,2',3'-O-tribenzoyluridine 在 吡啶 、 四氮唑 、 二氯乙酸 、 ammonium hydroxide 、 碘 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 5'-O-phosphoryl-1'-deoxy-2'-isoadenylyl-(3'->5')-uridine
  参考文献：
  名称：

  Synthetic Approaches to Nuclease-Resistant, Nonnatural Dinucleotides of Anti-Hiv Integrase Interest

  摘要：

  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.

  DOI：

  10.1080/15257770500265703

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.