1-(5'-amino-5'-carboxypentyl)pyrrole | 156539-32-1

• 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: 1-(5'-amino-5'-carboxypentyl)pyrrole
• 英文别名: N^ε-pyrrole-L-lysine；N-pyrrole-L-lysine；pyrK；(2s)-2-Amino-6-(1h-pyrrol-1-yl)hexanoic acid；(2S)-2-amino-6-pyrrol-1-ylhexanoic acid
• CAS: 156539-32-1
• 化学式: C₁₀H₁₆N₂O₂
• 分子量: 196.249
• InChiKey: KVCPIDDKLUDCQJ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  L-赖氨酸 、 丁二醛 以 aq. phosphate buffer 为溶剂， 生成 1-(5'-amino-5'-carboxypentyl)pyrrole
  参考文献：
  名称：

  抗坏血酸的自氧化介导赖氨酸 N-吡咯化

  摘要：

  摘要 将赖氨酸残基转化为N ε -吡咯-l-赖氨酸 (pyrK) 的蛋白质N-吡咯化是一种天然存在的共价修饰。吡咯化蛋白质具有与 DNA 染色剂（如 SYBR Green I (SG)）和抗 DNA 抗体结合的独特特性，表明产生 DNA 模拟蛋白的生理学相关修饰。吡咯化蛋白质的这些特性被认为与先天性和自身免疫反应有关。源自脂质过氧化的短链醛被认为参与了 pyrK 的形成。我们现在报告类似的赖氨酸N-吡咯化也发生在抗坏血酸金属催化的蛋白质氧化过程中。当人血清白蛋白 (HSA)在存在和不存在二十二碳六烯酸的情况下与 Fe 2+ /抗坏血酸盐一起孵育时，即使没有多不饱和脂肪酸，该蛋白质也会转化为 SG 结合蛋白。由 Fe 2+ /抗坏血酸盐形成的 SG 结合蛋白伴随着 pyrK 的形成，这也在抗坏血酸盐处理的血红蛋白中检测到。此外，抗坏血酸的金属催化氧化产生了吡咯化因子、乙醇醛和乙二醛。这些结果以及来自自身免疫倾向

  DOI：

  10.1080/10715762.2023.2174865

文献信息

• Characterization of the Products Formed during Microwave Irradiation of the Nonenzymic Browning Lysine/(E)-4,5-Epoxy-(E)-2-heptenal Model System
  作者：Francisco J. Hidalgo、Rosario Zamora

  DOI：10.1021/jf00052a033

  日期：1995.4

  Previous studies have shown that a lysine/(E)-4,5-epoxy-(E)-2-heptenal model system may help to elucidate the nonenzymatic browning produced in foods by lipid peroxidation products during microwave heating. As a continuation of those studies, this research was undertaken to isolate and characterize the different compounds that are produced in the above system in order to elucidate the mechanisms that take place at the molecular level upon microwave irradiation. Six pyrrole derivatives were isolated and characterized by H-1 and C-13 nuclear magnetic resonance spectroscopy and mass spectrometry. They were 1-[5'-amino-(1' and 5')-carboxypentyl]pyrrole (3 and 4, respectively), 1-[5'-amino-(1' and 5')-carboxypentyl]-2-(1''-hydroxypropyl)pyrrole (5 and 6, respectively), and 1-(5'-amino-1'-carboxypentyl)-2-[(Z and E)-1''-propenyl]pyrrole (7 and 8, respectively). Two of these compounds (7 and 8) were not previously found during thermic heating at low or moderate temperatures. A possible mechanism that explains the formation of all these compounds is suggested and discussed in relation to the formation of color and fluorescence in this system.