Kemp's anhydride acid | 146667-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Kemp's anhydride acid
• CAS: 146667-27-8
• 化学式: C₃₃H₃₄O₈
• 分子量: 558.628
• InChiKey: FXFYMDUZGJIJEA-VZRBIBDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.95
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  108.36
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Kemp's anhydride acid 在 吡啶 、 ammonium hydroxide 、 氯化亚砜 作用下， 生成 (1R,5S,7R)-1,5,7-Tris-benzyloxymethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylic acid phenylamide
  参考文献：
  名称：

  Molecular recognition in water: new receptors for adenine derivatives

  摘要：

  DOI：

  10.1021/ja00055a066
• 作为产物：
  描述：

  苄基氯甲基醚 在 氢氧化钾 、 lithium diisopropyl amide 作用下， 以 乙醇 、 xylene 为溶剂， 反应 5.25h， 生成 Kemp's anhydride acid
  参考文献：
  名称：

  Water-Soluble Receptors for Cyclic-AMP and Their Use for Evaluating Phosphate-Guanidinium Interactions

  摘要：

  A water-soluble receptor for adenosine derivatives was synthesized for the study of molecular recognition in aqueous solution. The modular receptor makes use of hydrophobic interactions, Watson-Crick and Hoogsteen hydrogen-bonding, and a phosphate-guanidinium electrostatic interaction to bind cyclic adenosine monophosphates. Measured binding affinities of 2',3/-cAMP are -3.65 and -3.26 kcal/mol at 51 and 501 mM ionic strength, respectively (H2O/D2O solution at 10 degrees C, pH 6.0). The phosphate-guanidinium interaction in this system is estimated to contribute on average 0.6 kcal/mol (51 mM ionic strength) and 0.3 kcal/mol (501 mM ionic strength) to binding. The maximum value of a phosphate-guanidinium electrostatic interaction is estimated to be 2.4 kcal/mol in water.

  DOI：

  10.1021/ja00087a013

文献信息

• Selective Recognition of Aromatic Amino Acids by a Molecular Cleft in Water
  作者：Joël F. Keller、Michal Valášek、Marcel Mayor

  DOI：10.1002/hlca.202300221

  日期：2024.2

  recognition of aromatic amino acids is highly desirable and may serve as a tool to facilitate drug discovery and enable fabrication of sensors for point-of-care monitoring in the context of phenylketonuria disease. This paper presents the synthesis and characterization of a water-soluble molecular cleft which is demonstrated to selectively bind aromatic amino acid guests over other amino acids in aqueous

  开发用于选择性识别芳香族氨基酸的水溶性宿主是非常可取的，并且可以作为促进药物发现和制造用于苯丙酮尿症疾病现场监测的传感器的工具。本文介绍了水溶性分子裂缝的合成和表征，该分子裂缝被证明可以在水介质中选择性地结合芳香族氨基酸客体，而不是其他氨基酸，与 ʟ-Phe 和 ʟ-Tyr 相比，ʟ-Trp 的优势约为 5 倍。通过1 H-NMR 滴定并辅以荧光滴定和等温滴定量热法研究主体/客体相互作用力。这里给出的结果为我们未来选择性识别和量化水介质中单个芳香族氨基酸的优化工作提供了一个起点。
• Energetics of a Low Barrier Hydrogen Bond in Nonpolar Solvents
  作者：Yoko Kato、Leticia M. Toledo、Julius Rebek

  DOI：10.1021/ja960288l

  日期：1996.1.1

  A measure of the strength of a low barrier hydrogen bond (LBHB) in apolar organic media was obtained using synthetic molecules derived from Kemp's triacid. The structures feature unusually rigid conformations that enforce intramolecular hydrogen bonds in a dicarboxylic acid, its corresponding acid-amide and their respective conjugate bases. Analysis of proton and deuterium NMR spectra established the formation of a LBHB in the conjugate base of the diacid and a conventional hydrogen bond in the conjugate base of the acid-amide. Through deprotonation equilibria with organic bases, it was determined that the conjugate base of the diacid was more stable than the conjugate base of the acid-amide by 2.4 kcal/mol in benzene and 1.4 kcal/mol in dichloromethane. These figures set the upper limits for the free energy of the additional stabilization arising from the LBHB at 25 degrees C. This value is far lower than many estimates but is closer to the recent determinations of Schwartz and Drueckhammer.