11-({2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethylcarbamoyl}-methyl)-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester | 957829-87-7

• 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-({2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethylcarbamoyl}-methyl)-1,4,8,11-tetraaza-cyclotetradecane-1,4,8-tricarboxylic acid tri-tert-butyl ester
• 英文别名: tritert-butyl 11-[2-[2-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]ethylamino]-2-oxoethyl]-1,4,8,11-tetrazacyclotetradecane-1,4,8-tricarboxylate
• CAS: 957829-87-7
• 化学式: C₃₉H₇₀N₈O₉S
• 分子量: 827.099
• InChiKey: MPLVVUUMZMWCMQ-OLWNVYNHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  217
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  11-({2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethylcarbamoyl}-methyl)-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92%的产率得到11-({2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethylcarbamoyl}-methyl)-1,4,8,11-tetraaza-cyclotetradecane tris(trifluoroacetate)
  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
• 作为产物：
  描述：

  1,4,8-三(叔丁氧碳酰)-1,4,8,11-四氮杂环十四烷 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 sodium carbonate 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 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 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 72.0h， 生成 11-({2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-4-yl)-pentanoylamino]-ethylcarbamoyl}-methyl)-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.