N5-[2-(N3-fluorenylmethyloxycarbonylthioureido)ethylcarbonyl]-N1-(tritylaminooxyacetyl)-1,5-diaminonaphthalene | 1166232-53-6

• 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: N5-[2-(N3-fluorenylmethyloxycarbonylthioureido)ethylcarbonyl]-N1-(tritylaminooxyacetyl)-1,5-diaminonaphthalene
• CAS: 1166232-53-6
• 化学式: C₅₀H₄₃N₅O₅S
• 分子量: 825.988
• InChiKey: AECLWAMYYMUEQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.03
• 重原子数：
  61.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  129.82
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N5-[2-(N3-fluorenylmethyloxycarbonylthioureido)ethylcarbonyl]-N1-(tritylaminooxyacetyl)-1,5-diaminonaphthalene 、 N-生物素-3,6-二氧杂辛烷-1,8-二胺 在 N,N-二异丙基乙胺 、 mercury dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51%的产率得到N5-[2-(N3-{2-[2-(2-biotinylaminoethoxy)ethoxy]ethyl}-N2-fluorenylmethyloxycarbonylguanidino)ethylcarbonyl]-N1-(tritylaminooxyacetyl)-1,5-diaminonaphthalene
  参考文献：
  名称：

  Construction of Highly Reactive Probes for Abasic Site Detection by Introduction of an Aromatic and a Guanidine Residue into an Aminooxy Group

  摘要：

  Abasic sites (AP sites) arise from hydrolysis of glycosidic bonds of DNA that is damaged by various external and internal processes; unrepaired AP sites give rise to genetic mutations. We have constructed highly reactive AID, site-detecting probes by introducing a hydrophobic and a hydrophilic residue in an aminooxy group. Synthesized probes containing either a naphthalene or a guanidine residue conjugate effectively with AP sites. In particular, a probe containing both functional groups shows the highest reaction rate, indicating that the hydrophobic and hydrophilic interactions act cooperatively in reaction with AP sites. The guanidine residue also contributes to the solubility of the molecules in aqueous media. The biotinylated probes provide much more sensitive detection of AP sites in genomic DNA than the conventional aldehyde-reactive probe.

  DOI：

  10.1021/ja904767k
• 作为产物：
  描述：

  N5-(2-aminoethylcarbonyl)-N1-(tritylaminooxyacetyl)-1,5-diaminonaphthalene 、 Fmoc-异硫氰酸 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 以94%的产率得到N5-[2-(N3-fluorenylmethyloxycarbonylthioureido)ethylcarbonyl]-N1-(tritylaminooxyacetyl)-1,5-diaminonaphthalene
  参考文献：
  名称：

  Construction of Highly Reactive Probes for Abasic Site Detection by Introduction of an Aromatic and a Guanidine Residue into an Aminooxy Group

  摘要：

  Abasic sites (AP sites) arise from hydrolysis of glycosidic bonds of DNA that is damaged by various external and internal processes; unrepaired AP sites give rise to genetic mutations. We have constructed highly reactive AID, site-detecting probes by introducing a hydrophobic and a hydrophilic residue in an aminooxy group. Synthesized probes containing either a naphthalene or a guanidine residue conjugate effectively with AP sites. In particular, a probe containing both functional groups shows the highest reaction rate, indicating that the hydrophobic and hydrophilic interactions act cooperatively in reaction with AP sites. The guanidine residue also contributes to the solubility of the molecules in aqueous media. The biotinylated probes provide much more sensitive detection of AP sites in genomic DNA than the conventional aldehyde-reactive probe.

  DOI：

  10.1021/ja904767k