6-[(6-azidohexanoyl)amino]caproic acid | 866363-71-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-[(6-azidohexanoyl)amino]caproic acid
• 英文别名: N3-Aca-Aca-OH；6-(6-azidohexanoylamino)hexanoic acid
• CAS: 866363-71-5
• 化学式: C₁₂H₂₂N₄O₃
• 分子量: 270.332
• InChiKey: AEPIYQTVXFLWBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  80.8
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

N3 Aca Aca OH是一种含有叠氮化物基团的点击化学试剂。点击化学在核酸、脂质、蛋白质及其他分子间的结合中具有巨大潜力，且由于其高产率、高特异性和简单性等特点，在多个研究领域已被广泛应用。

反应信息

• 作为反应物：
  描述：

  6-[(6-azidohexanoyl)amino]caproic acid 、 N-羟基丁二酰亚胺 在 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到6-[(6-azidohexanoyl)amino]caproic acid succinimidyl ester
  参考文献：
  名称：

  On the Preparation of Carbohydrate−Protein Conjugates Using the Traceless Staudinger Ligation

  摘要：

  The nature of a linker used for preparing glycoconjugate vaccines is of utmost importance as it may lead to immunogenic biomolecules. We report the conjugation of carbohydrate haptens to protein carriers leading to potential vaccines using the traceless Staudinger ligation. The ligation relies on the selective transfer of a phosphane substituent to an azide to form a native amide bond in the final product upon release of an oxidized phosphane byproduct. We designed new phosphino-functionalized cross-linkers suitable for protein carrier derivatization. We evaluated their utility in preparing conjugates using both synthetic and purified bacterial carbohydrates. The use of a borane-protected phosphane which is deprotected at the time of the ligation reaction led to the best results observed thus far in terms of stability toward oxidation and reactivity.

  DOI：

  10.1021/jo0505472
• 作为产物：
  描述：

  6-溴己酸 在 sodium azide 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 6-[(6-azidohexanoyl)amino]caproic acid
  参考文献：
  名称：

  On the Preparation of Carbohydrate−Protein Conjugates Using the Traceless Staudinger Ligation

  摘要：

  The nature of a linker used for preparing glycoconjugate vaccines is of utmost importance as it may lead to immunogenic biomolecules. We report the conjugation of carbohydrate haptens to protein carriers leading to potential vaccines using the traceless Staudinger ligation. The ligation relies on the selective transfer of a phosphane substituent to an azide to form a native amide bond in the final product upon release of an oxidized phosphane byproduct. We designed new phosphino-functionalized cross-linkers suitable for protein carrier derivatization. We evaluated their utility in preparing conjugates using both synthetic and purified bacterial carbohydrates. The use of a borane-protected phosphane which is deprotected at the time of the ligation reaction led to the best results observed thus far in terms of stability toward oxidation and reactivity.

  DOI：

  10.1021/jo0505472