N5-[2-(N3-{2-[2-(2-biotinylaminoethoxy)ethoxy]ethyl}guanidino)ethylcarbonyl]-N1-(aminooxyacetyl)-1,5-diaminonaphthalene trifluoroacetic acid | 1187179-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: N5-[2-(N3-{2-[2-(2-biotinylaminoethoxy)ethoxy]ethyl}guanidino)ethylcarbonyl]-N1-(aminooxyacetyl)-1,5-diaminonaphthalene trifluoroacetic acid
• CAS: 1187179-38-9
• 化学式: C₂HF₃O₂*C₃₂H₄₇N₉O₇S
• 分子量: 815.871
• InChiKey: IAYOWXMGOBKSRL-IYGAPYOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  56.0
• 可旋转键数：
  21.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  267.35
• 氢给体数：
  10.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  N5-[2-(N3-{2-[2-(2-biotinylaminoethoxy)ethoxy]ethyl}-N2-fluorenylmethyloxycarbonylguanidino)ethylcarbonyl]-N1-(aminooxyacetyl)-1,5-diaminonaphthalene 在 哌啶 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 以33%的产率得到N5-[2-(N3-{2-[2-(2-biotinylaminoethoxy)ethoxy]ethyl}guanidino)ethylcarbonyl]-N1-(aminooxyacetyl)-1,5-diaminonaphthalene trifluoroacetic acid
  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