5'-O-(4,4'-dimethoxytrityl)-N⁶-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite) | 1076168-10-9

• 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: 5'-O-(4,4'-dimethoxytrityl)-N⁶-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)
• CAS: 1076168-10-9
• 化学式: C₅₈H₅₉N₈O₇P
• 分子量: 1011.13
• InChiKey: AYROXJXCUFHQNO-XZPVEWMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.02
• 重原子数：
  74.0
• 可旋转键数：
  20.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  167.14
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  5'-O-(4,4'-dimethoxytrityl)-N⁶-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine 、 2-氰乙基N,N-二异丙基氯亚磷酰胺 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以70%的产率得到5'-O-(4,4'-dimethoxytrityl)-N⁶-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine 3'-(2-cyanoethyl N,N-diisopropylphosphoramidite)
  参考文献：
  名称：

  Hybridization-dependent fluorescence of oligodeoxynucleotides incorporating new pyrene-modified adenosine residues

  摘要：

  We report the synthesis and properties of oligonucleotides incorporating N(6)-[N-(pyren-1-ylmethyl) carbamoyl]deoxyadenosine (dA(pymcm)). We designed the ODN which incorporated two consecutive dA(pymcm) residues. It was revealed that on hybridization with the target DNA and RNA oligomers, the fluorescence spectra of ODNs having two consecutive dA(pymcm) molecules near the 5'-terminal position can change from the pyrene monomer emission to the excimer, depending on the chain length of the target DNA and RNA. These results indicated that dA(pymcm)-modified ODNs can be used as interesting hybridization sensors that are sensitive to the size of the target strand. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.05.042