| 1097194-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 1097194-53-0
• 化学式: C₇₃H₇₂N₁₀O₁₈S
• 分子量: 1409.5
• InChiKey: WMZHTIRPCQEORQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.04
• 重原子数：
  102.0
• 可旋转键数：
  21.0
• 环数：
  24.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  337.65
• 氢给体数：
  3.0
• 氢受体数：
  25.0

反应信息

• 作为产物：
  描述：

  3-叠氮丙酸 、 C₆₇H₆₂N₄O₁₄S 在 2,6-二甲基吡啶 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 二甲基亚砜 为溶剂， 以51%的产率得到
  参考文献：
  名称：

  Enantiopure cryptophane-¹²⁹Xe nuclear magnetic resonance biosensors targeting carbonic anhydrase

  摘要：

  The (+) and (-) enantiomers for a cryptophane-7-bond-linker-benzenesulfonamide biosensor (C7B) were synthesised and their chirality was confirmed by electronic circular dichroism spectroscopy. Biosensor binding to carbonic anhydrase II (CAII) was characterised for both enantiomers by hyperpolarised (HP) Xe-129 NMR spectroscopy. Our previous study of the racemic (+/-) C7B biosensor-CAII complex [Chambers, J.M.; Hill, P.A.; Aaron, J.A.; Han, Z.H.; Christianson, D.W.; Kuzma, N.N.; Dmochowski, I.J. J. Am. Chem. Soc.2009, 131, 563-569] identified two 'bound' Xe-129@C7B peaks by HP Xe-129 NMR (at 71 and 67ppm, relative to 'free' biosensor at 64ppm), which led to the initial hypothesis that (+) and (-) enantiomers produce diastereomeric peaks when coordinated to Zn2+ at the chiral CAII active site. Unexpectedly, the single enantiomers complexed with CAII also identified two 'bound' Xe-129@C7B peaks: (+) 72, 68ppm and (-) 68, 67ppm. These results are consistent with X-ray crystallographic evidence for benzenesulfonamide inhibitors occupying a second site near the CAII surface. As illustrated by our studies of this model protein-ligand interaction, HP Xe-129 NMR spectroscopy can be useful for identifying supramolecular assemblies in solution.

  DOI：

  10.1080/10610278.2014.906601

文献信息

• Cryptophane Xenon-129 Nuclear Magnetic Resonance Biosensors Targeting Human Carbonic Anhydrase
  作者：Jennifer M. Chambers、P. Aru Hill、Julie A. Aaron、Zhaohui Han、David W. Christianson、Nicholas N. Kuzma、Ivan J. Dmochowski

  DOI：10.1021/ja806092w

  日期：2009.1.21

  eight-bond-linked biosensor containing a single xenon atom in the CAII active site. Biosensor dissociation constants (K(d) = 20-110 nM) were determined by isothermal titration calorimetry (ITC) for isozymes CA I and II. The biosensor-CA complexes yielded "bound" hyperpolarized (129)Xe NMR resonances of narrow line width that were shifted by 3.0-7.5 ppm downfield, signifying much larger shifts than seen previously

  (129)Xe NMR 生物传感器是用于早期疾病检测的有前景的试剂，特别是当它们与目标生物分子的相互作用可以扰乱 (129)Xe 化学位移，远远超出临床 MRI 的典型场不均匀性时。我们引入人碳酸酐酶（CA）作为单结合位点酶来研究氙生物传感器-蛋白质相互作用。用不同长度的对苯磺酰胺连接体取代与氙结合的密码烷，产生具有单一 (129)Xe NMR 共振的非非对映生物传感器。 X 射线晶体学证实了 CAII 活性位点上含有单个氙原子的八键连接生物传感器的结合。通过等温滴定量热法 (ITC) 测定同工酶 CA I 和 II 的生物传感器解离常数 (K(d) = 20-110 nM)。生物传感器-CA复合物产生了窄线宽的“结合”超极化(129)Xe NMR共振，其向低场偏移了3.0-7.5 ppm，这意味着比之前看到的偏移大得多。此外，尽管 CA I 和 II 的结构相似，但同工酶特异性化学位移明