(1S,3R,4R,7S)-3-(8-bromoadenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane | 1275611-33-0

• 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: (1S,3R,4R,7S)-3-(8-bromoadenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
• CAS: 1275611-33-0
• 化学式: C₁₁H₁₂BrN₅O₄
• 分子量: 358.151
• InChiKey: WYZSWDWVCFHRNW-JUQFDLSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  128.54
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,7S)-3-(8-bromoadenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 在 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 (1S,3R,4R,7S)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[8-(2-(1-pyrenyl)ethynyl)adenin-9-yl]-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis, Hybridization Characteristics, and Fluorescence Properties of Oligonucleotides Modified with Nucleobase-Functionalized Locked Nucleic Acid Adenosine and Cytidine Monomers

  摘要：

  Conformationally restricted nucleotides such as locked nucleic acid (LNA) are very popular as affinity-, specificity-, and stability-enhancing modifications in oligonucleotide chemistry to produce probes for nucleic acid targeting applications in molecular biology, biotechnology, and medicinal chemistry. Considerable efforts have been devoted in recent years to optimize the biophysical properties of LNA through additional modification of the sugar skeleton. We recently introduced C5-functionalization of LNA uridines as an alternative and synthetically more straightforward approach to improve the biophysical properties of LNA. In the present work, we set out to test the generality of this concept by studying the characteristics of oligonudeotides modified with four different C5-functionalized LNA cytidine and C8-functionalized LNA adenosine monomers. The results strongly suggest that C5-functionalization of LNA pyrimidines is indeed a viable approach for improving the binding affinity, target specificity, and/or enzymatic stability of LNA-modified ONs, whereas C8-functionalization of LNA adenosines is detrimental to binding affinity and specificity. These insights will impact the future design of conformationally restricted nucleotides for nucleic acid targeting applications.

  DOI：

  10.1021/jo500994c
• 作为产物：
  描述：

  (1S,3R,4R,7S)-3-(adenine-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane 在 溴 作用下， 以 1,4-二氧六环 为溶剂， 以85%的产率得到(1S,3R,4R,7S)-3-(8-bromoadenin-9-yl)-7-hydroxy-1-hydroxymethyl-2,5-dioxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  [EN] NUCLEOBASE-FUNCTIONALIZED CONFORMATIONALLY RESTRICTED NUCLEOTIDES AND OLIGONUCLEOTIDES FOR TARGETING NUCLEIC ACIDS
  [FR] NUCLÉOTIDES ET OLIGONUCLÉOTIDES À CONFORMATION RESTREINTE À FONCTIONNALITÉ NUCLÉOBASE POUR CIBLER DES ACIDES NUCLÉIQUES

  摘要：

  公开号：

  WO2011032034A3