N-(2-((3-(propargylamino)-3-oxopropyl)disulfanyl)ethyl)-1-(5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)-pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide | 1260247-54-8

• 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: N-(2-((3-(propargylamino)-3-oxopropyl)disulfanyl)ethyl)-1-(5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)-pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide
• 英文别名: Biotin-PEG(4)-SS-Alkyne；5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[2-[2-[2-[3-oxo-3-[2-[[3-oxo-3-(prop-2-ynylamino)propyl]disulfanyl]ethylamino]propoxy]ethoxy]ethoxy]ethoxy]ethyl]pentanamide
• CAS: 1260247-54-8
• 化学式: C₂₉H₄₉N₅O₈S₃
• 分子量: 691.935
• InChiKey: GWOIFEYTEHHIJC-QONNDPFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  45.0
• 可旋转键数：
  28.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  165.35
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  2,5-dioxopyrrolidin-1-yl 3-{[2-(1-{5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanamido}-3,6,9,12-tetraoxapentadecan-15-amido)ethyl]disulfanyl}propanoate 、 炔丙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到N-(2-((3-(propargylamino)-3-oxopropyl)disulfanyl)ethyl)-1-(5-((3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazol-4-yl)-pentanamido)-3,6,9,12-tetraoxapentadecan-15-amide
  参考文献：
  名称：

  Cleavable Biotin Probes for Labeling of Biomolecules via Azide−Alkyne Cycloaddition

  摘要：

  The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na2S2O4, 2% HOCH2CH2SH, 10% HCO2H, 95% CF3CO2H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO2H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies.

  DOI：

  10.1021/ja1083909

文献信息

• Cleavable Biotin Probes for Labeling of Biomolecules via Azide−Alkyne Cycloaddition
  作者：Janek Szychowski、Alborz Mahdavi、Jennifer J. L. Hodas、John D. Bagert、John T. Ngo、Peter Landgraf、Daniela C. Dieterich、Erin M. Schuman、David A. Tirrell

  DOI：10.1021/ja1083909

  日期：2010.12.29

  The azide-alkyne cycloaddition provides a powerful tool for bio-orthogonal labeling of proteins, nucleic acids, glycans, and lipids. In some labeling experiments, e.g., in proteomic studies involving affinity purification and mass spectrometry, it is convenient to use cleavable probes that allow release of labeled biomolecules under mild conditions. Five cleavable biotin probes are described for use in labeling of proteins and other biomolecules via azide-alkyne cycloaddition. Subsequent to conjugation with metabolically labeled protein, these probes are subject to cleavage with either 50 mM Na2S2O4, 2% HOCH2CH2SH, 10% HCO2H, 95% CF3CO2H, or irradiation at 365 nm. Most strikingly, a probe constructed around a dialkoxydiphenylsilane (DADPS) linker was found to be cleaved efficiently when treated with 10% HCO2H for 0.5 h. A model green fluorescent protein was used to demonstrate that the DADPS probe undergoes highly selective conjugation and leaves a small (143 Da) mass tag on the labeled protein after cleavage. These features make the DADPS probe especially attractive for use in biomolecular labeling and proteomic studies.