(2S,2'S,2''S)-t-Butyl-2,2',2''-[(2S,5S,8S,11S)-10-((S)-1-(benzyloxy)-1-oxopropan-2-yl)-2,5,8,11-tetramethyl-1,4,7,10-tetraazacyclododecane-1,4,7-triyl]-tripropanoate | 1192364-54-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,2'S,2''S)-t-Butyl-2,2',2''-[(2S,5S,8S,11S)-10-((S)-1-(benzyloxy)-1-oxopropan-2-yl)-2,5,8,11-tetramethyl-1,4,7,10-tetraazacyclododecane-1,4,7-triyl]-tripropanoate
• 英文别名: tM4DOTMA-Bn；2,5,8,11-Tetramethyl Benzyl Ester Tri-t-Butyl Ester Cyclen；benzyl (2S)-2-[(2S,5S,8S,11S)-2,5,8,11-tetramethyl-4,7,10-tris[(2S)-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]-1,4,7,10-tetrazacyclododec-1-yl]propanoate
• CAS: 1192364-54-7
• 化学式: C₄₃H₇₄N₄O₈
• 分子量: 775.083
• InChiKey: FMZMTLLGDAYGBP-DZCXQCEKSA-N

物化性质

• 沸点：
  725.2±60.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.08
• 重原子数：
  55.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  118.16
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2S,2'S,2''S)-t-Butyl-2,2',2''-[(2S,5S,8S,11S)-10-((S)-1-(benzyloxy)-1-oxopropan-2-yl)-2,5,8,11-tetramethyl-1,4,7,10-tetraazacyclododecane-1,4,7-triyl]-tripropanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 20.0h， 生成 (S)-2-[(2S,5S,8S,11S)-4,7,10-tris((S)-1-t-butoxy-1-oxopropan-2-yl)-2,5,8,11-tetramethyl-1,4,7,10-tetraazacyclododecane-1-yl]-propanoic acid
  参考文献：
  名称：

  DOTA-M8: An Extremely Rigid, High-Affinity Lanthanide Chelating Tag for PCS NMR Spectroscopy

  摘要：

  A new lanthanide chelating tag (M8) for paramagnetic labeling of biomolecules is presented, which is based on an eight-fold, stereoselectively methyl-substituted DOTA that can be covalently linked to the host molecule by a single disulfide bond. The steric overcrowding of the DOTA scaffold leads to an extremely rigid, kinetically and chemically inert lanthanide chelator Its steric bulk restricts the motion of the tag relative to the host molecule. These properties result in very large pseudocontact shifts (>5 ppm) and residual dipolar couplings (>20 Hz) for Dy-M8 linked to ubiquitin, which are unprecedented for a small, single-point-attachment tag. Such large pseudocontact shifts should be well detectable even for larger proteins and distances beyond similar to 50 angstrom. Due to its exceptionally high stability and lanthanide affinity M8 can be used under extreme chemical or physical conditions, such as those applied for protein denaturation, or when it is undesirable that buffer or protein react with excess lanthanide ions.

  DOI：

  10.1021/ja903233w
• 作为产物：
  描述：

  tert-butyl (R)-2-(((trifluoromethyl)sulfonyl)oxy)propanoate 、 (S)-benzyl 2-[(2S,5S,8S,11S)-2,5,8,11-tetramethyl-,1,4,7,10-tetramethyl-1,4,7,10-tetraazacyclododecane-1-yl]-propanoate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以90%的产率得到(2S,2'S,2''S)-t-Butyl-2,2',2''-[(2S,5S,8S,11S)-10-((S)-1-(benzyloxy)-1-oxopropan-2-yl)-2,5,8,11-tetramethyl-1,4,7,10-tetraazacyclododecane-1,4,7-triyl]-tripropanoate
  参考文献：
  名称：

  DOTA-M8: An Extremely Rigid, High-Affinity Lanthanide Chelating Tag for PCS NMR Spectroscopy

  摘要：

  A new lanthanide chelating tag (M8) for paramagnetic labeling of biomolecules is presented, which is based on an eight-fold, stereoselectively methyl-substituted DOTA that can be covalently linked to the host molecule by a single disulfide bond. The steric overcrowding of the DOTA scaffold leads to an extremely rigid, kinetically and chemically inert lanthanide chelator Its steric bulk restricts the motion of the tag relative to the host molecule. These properties result in very large pseudocontact shifts (>5 ppm) and residual dipolar couplings (>20 Hz) for Dy-M8 linked to ubiquitin, which are unprecedented for a small, single-point-attachment tag. Such large pseudocontact shifts should be well detectable even for larger proteins and distances beyond similar to 50 angstrom. Due to its exceptionally high stability and lanthanide affinity M8 can be used under extreme chemical or physical conditions, such as those applied for protein denaturation, or when it is undesirable that buffer or protein react with excess lanthanide ions.

  DOI：

  10.1021/ja903233w