N,N'-di(p-nitrobenzoyl)-L-cystine | 5330-87-0

• 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: N,N'-di(p-nitrobenzoyl)-L-cystine
• 英文别名: N,N'-bis-(4-nitro-benzoyl)-L-cystine；N,N'-Bis-(4-nitro-benzoyl)-L-cystin；Bz(4-NO2)-Cys(1)-OH.Bz(4-NO2)-Cys(1)-OH；(2R)-3-[[(2R)-2-carboxy-2-[(4-nitrobenzoyl)amino]ethyl]disulfanyl]-2-[(4-nitrobenzoyl)amino]propanoic acid
• CAS: 5330-87-0
• 化学式: C₂₀H₁₈N₄O₁₀S₂
• 分子量: 538.516
• InChiKey: UVYFOLWELOVJQB-HOTGVXAUSA-N

物化性质

• 沸点：
  900.4±65.0 °C(Predicted)
• 密度：
  1.590±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  275
• 氢给体数：
  4
• 氢受体数：
  12

安全信息

• 海关编码：
  2930909090

反应信息

• 作为产物：
  描述：

  L-胱氨酸 、 4-硝基苯甲酰氯 在 sodium hydroxide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 24.0h， 以13%的产率得到N,N'-di(p-nitrobenzoyl)-L-cystine
  参考文献：
  名称：

  Anatomy of a Gel. Amino Acid Derivatives That Rigidify Water at Submillimolar Concentrations

  摘要：

  On the basis of suggestive X-ray data, 14 aroyl L-cystine derivatives were designed, synthesized, and examined for their ability to gelate water. Several members of this amino acid family are remarkably effective aqueous gelators (the best being one that can rigidify aqueous solutions at 0.25 mM, ca. 0.01%, in less than 30 s!). A few of the analogues separate from water as crystals, indicating a close relationship between gelation and crystallization. All effective gelators self-assemble into fibrous structures that entrain the solvent in the capillary spaces among them. Hydrogen-bonding sites on the compounds that might stabilize the fibers were identified from specific substitutions that replace a hydrogen donor with a methyl group, enhance the hydrogen-accepting ability of a carbonyl oxygen, or promote the hydrogen-donating, ability of an amide proton. The structural variations were characterized via minimal gelation concentrations and times, X-ray crystallography, light and electron microscopy, rheology, and calorimetry. The multiple techniques, applied to the diverse compounds, allowed an extensive search into the basis of gelation. It was learned, for example, that the compound with the lowest minimum gelator concentration and time also has one of the weakest gels (i.e., it has a low elastic modulus). This is attributed to kinetic effects that perturb the length of the fibers. It was also argued that pi/pi stacking, the carboxyl carbonyl (but not the carboxyl proton), and solubility factors all contribute to the stability of a fiber. Polymorphism also plays a role. Rheological studies at different temperatures show that certain gels are stable to a 1-Hz, 3-Pa oscillating shear stress at temperatures as high as 90 degreesC. Other gels have a "catastrophic" break at lower temperatures. Calorimetric data indicate a smooth transition from gel to sol as the temperature is increased. These and other issues are discussed in this "anatomy" of a gel.

  DOI：

  10.1021/ja0016811

文献信息

• Inoue, Rikagaku Kenkyusho Iho, 1929, vol. 8, p. 647,650
  作者：Inoue

  DOI：——

  日期：——
• Anatomy of a Gel. Amino Acid Derivatives That Rigidify Water at Submillimolar Concentrations
  作者：Fredric M. Menger、Kevin L. Caran

  DOI：10.1021/ja0016811

  日期：2000.11.1

  On the basis of suggestive X-ray data, 14 aroyl L-cystine derivatives were designed, synthesized, and examined for their ability to gelate water. Several members of this amino acid family are remarkably effective aqueous gelators (the best being one that can rigidify aqueous solutions at 0.25 mM, ca. 0.01%, in less than 30 s!). A few of the analogues separate from water as crystals, indicating a close relationship between gelation and crystallization. All effective gelators self-assemble into fibrous structures that entrain the solvent in the capillary spaces among them. Hydrogen-bonding sites on the compounds that might stabilize the fibers were identified from specific substitutions that replace a hydrogen donor with a methyl group, enhance the hydrogen-accepting ability of a carbonyl oxygen, or promote the hydrogen-donating, ability of an amide proton. The structural variations were characterized via minimal gelation concentrations and times, X-ray crystallography, light and electron microscopy, rheology, and calorimetry. The multiple techniques, applied to the diverse compounds, allowed an extensive search into the basis of gelation. It was learned, for example, that the compound with the lowest minimum gelator concentration and time also has one of the weakest gels (i.e., it has a low elastic modulus). This is attributed to kinetic effects that perturb the length of the fibers. It was also argued that pi/pi stacking, the carboxyl carbonyl (but not the carboxyl proton), and solubility factors all contribute to the stability of a fiber. Polymorphism also plays a role. Rheological studies at different temperatures show that certain gels are stable to a 1-Hz, 3-Pa oscillating shear stress at temperatures as high as 90 degreesC. Other gels have a "catastrophic" break at lower temperatures. Calorimetric data indicate a smooth transition from gel to sol as the temperature is increased. These and other issues are discussed in this "anatomy" of a gel.