(2R,2'R,2''R)-2,2',2''-((2S,5S,8S,11S)-2,5,8,11-tetramethyl-10-((R)-1-oxo-1-((2-(pyridin-2yldithio)ethyl)amino)propan-2-yl)-1,4,7,10-tetraazacyclo-dodecane-1,4,7-triyl)tripropanoic acid | 1192364-62-7

• 英文名称: (2R,2'R,2''R)-2,2',2''-((2S,5S,8S,11S)-2,5,8,11-tetramethyl-10-((R)-1-oxo-1-((2-(pyridin-2yldithio)ethyl)amino)propan-2-yl)-1,4,7,10-tetraazacyclo-dodecane-1,4,7-triyl)tripropanoic acid
• CAS: 1192364-62-7
• 化学式: C₃₁H₅₂N₆O₇S₂
• 分子量: 684.922
• InChiKey: BVEXZTXAUQXVNC-HITYTLSWSA-N

反应信息

• 作为反应物：
  描述：

  gadolinium(III) oxochloride 、 (2R,2'R,2''R)-2,2',2''-((2S,5S,8S,11S)-2,5,8,11-tetramethyl-10-((R)-1-oxo-1-((2-(pyridin-2yldithio)ethyl)amino)propan-2-yl)-1,4,7,10-tetraazacyclo-dodecane-1,4,7-triyl)tripropanoic acid 以 aq. acetate buffer 为溶剂， 生成 [Gd((2R,2'R,2''R)-2,2',2''-((2S,5S,8S,11S)-2,5,8,11-tetramethyl-10-((S)-1-oxo-1-((2-(pyridin-2yldithio)ethyl)amino)propan-2-yl)-1,4,7,10-tetraazacyclo-dodecane-1,4,7-triyl)tripropanate)]
  参考文献：
  名称：

  Gd(III) complexes for electron–electron dipolar spectroscopy: Effects of deuteration, pH and zero field splitting

  摘要：

  Spectral parameters of Gd(III) complexes are intimately linked to the performance of the Gd(III)nitroxide or Gd(III)-Gd(III) double electron-electron resonance (DEER or PELDOR) techniques, as well as to that of relaxation induced dipolar modulation enhancement (RIDME) spectroscopy with Gd(III) ions. These techniques are of interest for applications in structural biology, since they can selectively detect site-to-site distances in biomolecules or biomolecular complexes in the nanometer range. Here we report relaxation properties, echo detected EPR spectra, as well as the magnitude of the echo reduction effect in Gd(III)-nitroxide DEER for a series of Gadolinium(III) complexes with chelating agents derived from tetraazacyclododecane. We observed that solvent deuteration does not only lengthen the relaxation times of Gd(III) centers but also weakens the DEER echo reduction effect. Both of these phenomena lead to an improved signal-to-noise ratios or, alternatively, longer accessible distance range in pulse EPR measurements. The presented data enrich the knowledge on paramagnetic Gd(III) chelate complexes in frozen solutions, and can help optimize the experimental conditions for most types of the pulse measurements of the electron-electron dipolar interactions. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jmr.2015.08.009
• 作为产物：
  描述：

  在 茴香硫醚 、 水 、 三氟乙酸 作用下， 反应 5.0h， 生成 (2R,2'R,2''R)-2,2',2''-((2S,5S,8S,11S)-2,5,8,11-tetramethyl-10-((R)-1-oxo-1-((2-(pyridin-2yldithio)ethyl)amino)propan-2-yl)-1,4,7,10-tetraazacyclo-dodecane-1,4,7-triyl)tripropanoic 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