3',5'-O-bis(tert-butyldimethylsilyl)-N6-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine | 1076168-04-1

• 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: 3',5'-O-bis(tert-butyldimethylsilyl)-N6-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine
• 英文别名: 3',5'-O-bis(tert-butyldimethylsilyl)-N⁶-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine
• CAS: 1076168-04-1
• 化学式: C₄₀H₅₂N₆O₄Si₂
• 分子量: 737.062
• InChiKey: XDFHNXYBABHTBD-DCMFLLSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.75
• 重原子数：
  52.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  112.42
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3',5'-O-bis(tert-butyldimethylsilyl)-N6-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine 在 triethylamine trihydrofluoride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 1-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]-3-(pyren-1-ylmethyl)urea
  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
• 作为产物：
  描述：

  、 9-((2R,4S,5R)-4-((叔丁基二甲基硅烷基)氧基)-5-(((叔丁基二甲基硅烷基)氧基)甲基)四氢呋喃-2-基)-9H-嘌呤-6-胺 在 吡啶 作用下， 反应 2.0h， 以78%的产率得到3',5'-O-bis(tert-butyldimethylsilyl)-N6-[N-(pyren-1-ylmethyl)carbamoyl]deoxyadenosine
  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