11-{3-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-propyl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester | 957829-83-3

• 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: 11-{3-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-propyl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester
• 英文别名: 11-{3-[5-(2-oxohexahydrothieno[3,4-d]imidazol-4-yl)pentanoylamino]propyl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester；tritert-butyl 11-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propyl]-1,4,8,11-tetrazacyclotetradecane-1,4,8-tricarboxylate
• CAS: 957829-83-3
• 化学式: C₃₈H₆₉N₇O₈S
• 分子量: 784.074
• InChiKey: XVJBIFLNKFXSSU-QMOZSOIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  54
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  187
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  11-{3-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-propyl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester 、 三氟乙酸 以 二氯甲烷 为溶剂， 以100%的产率得到11-{3-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-propyl}-1,4,8,11-tetraaza-cyclotetradecane tris(trifluoroacetate)
  参考文献：
  名称：

  响应性金属配合物：基于点击的“变构蝎形”配合物允许通过EPR / ENDOR光谱检测生物识别事件

  摘要：

  点击检测！具有三唑蝎配体的氮杂大环配合物很容易组装，如生物素功能化的环蛋白衍生物所示。亲和素与侧基配体的结合会干扰三唑与金属的配位（请参见方案）。可以通过EPR和ENDOR光谱法灵敏地检测到此事件，这证实了抗生物素蛋白结合后轴向三唑氮供体的损失。该一般策略可能在成像和治疗中具有广泛的应用。

  DOI：

  10.1002/chem.200802425
• 作为产物：
  描述：

  11-(3-benzyloxycarbonylamino-propyl)-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 40.0h， 生成 11-{3-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-propyl}-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester
  参考文献：
  名称：

  Effective Methods for the Biotinylation of Azamacrocycles

  摘要：

  The biotin-(strept)avidin interaction remains a gold standard of model biological recognition events. The biotinylation of azarnacrocycles permits the investigation of signal transduction between this recognition event and the metal center of an azamacrocycle complex, of wide potential interest in biosensing. There are no generally applicable procedures in the literature for such functionalizations. We report here a comprehensive investigation into the attachment of biotin to TACN, cyclen, and cyclam.. Effective methods have been found for each ring. The efficacy of the functionalization is critically dependent on the nature of the azarnacrocycle.

  DOI：

  10.1021/jo071175v

文献信息

• Effective Methods for the Biotinylation of Azamacrocycles
  作者：Sara J. Krivickas、Emiliano Tamanini、Matthew H. Todd、Michael Watkinson

  DOI：10.1021/jo071175v

  日期：2007.10.1

  The biotin-(strept)avidin interaction remains a gold standard of model biological recognition events. The biotinylation of azarnacrocycles permits the investigation of signal transduction between this recognition event and the metal center of an azamacrocycle complex, of wide potential interest in biosensing. There are no generally applicable procedures in the literature for such functionalizations. We report here a comprehensive investigation into the attachment of biotin to TACN, cyclen, and cyclam.. Effective methods have been found for each ring. The efficacy of the functionalization is critically dependent on the nature of the azarnacrocycle.
• Responsive Metal Complexes: A Click-Based “Allosteric Scorpionate” Complex Permits the Detection of a Biological Recognition Event by EPR/ENDOR Spectroscopy
  作者：Emiliano Tamanini、Stephen E. J. Rigby、Majid Motevalli、Matthew H. Todd、Michael Watkinson

  DOI：10.1002/chem.200802425

  日期：2009.4.6

  Click to detect! Azamacrocyclic complexes with a triazole scorpion ligand may be easily assembled, as shown for a biotin‐functionalised cyclam derivative. Coordination of the triazole to the metal is perturbed by the binding of avidin to the pendant ligand (see scheme). This event can be sensitively detected with EPR and ENDOR spectroscopy, which confirm the loss of the axial triazole nitrogen donor

  点击检测！具有三唑蝎配体的氮杂大环配合物很容易组装，如生物素功能化的环蛋白衍生物所示。亲和素与侧基配体的结合会干扰三唑与金属的配位（请参见方案）。可以通过EPR和ENDOR光谱法灵敏地检测到此事件，这证实了抗生物素蛋白结合后轴向三唑氮供体的损失。该一般策略可能在成像和治疗中具有广泛的应用。