(2S)-1-(quinolin-6-ylcarbamoyl)pyrrolidine-2-carboxylic acid | 150331-60-5

• 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: (2S)-1-(quinolin-6-ylcarbamoyl)pyrrolidine-2-carboxylic acid
• CAS: 150331-60-5
• 化学式: C₁₅H₁₅N₃O₃
• 分子量: 285.302
• InChiKey: ICOJMKASMOSKSV-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[(6-喹啉基氨基甲酰)氧基]-2,5-吡咯烷二酮 、 L-脯氨酸 以 乙腈 为溶剂， 生成 (2S)-1-(quinolin-6-ylcarbamoyl)pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  通过前驱体离子扫描液相色谱/串联质谱法对衍生的氨基酸进行核磁共振研究，确定蛋白质的同位素标记

  摘要：

  已经开发出一种使用液相色谱/串联质谱法（LC / MS / MS）定量蛋白质同位素标记的方法，用于蛋白质核磁共振（NMR）研究。NMR依靠特定的同位素核（例如13 C和15 N）进行检测，因此，同位素标记是蛋白质深入结构表征之前的重要样品制备步骤。这项研究的目的是开发一种鲁棒的定量测定方法，以评估蛋白质中的同位素标记，同时保留有关单个氨基酸标记程度的信息。

  DOI：

  10.1002/rcm.6204

文献信息

• Determination of isotopic labeling of proteins by precursor ion scanning liquid chromatography/tandem mass spectrometry of derivatized amino acids applied to nuclear magnetic resonance studies
  作者：André LeBlanc、Alexandre A. Arnold、Bertrand Genard、Jean-Bruno Nadalini、Marc-Olivier Séguin Heine、Isabelle Marcotte、Réjean Tremblay、Lekha Sleno

  DOI：10.1002/rcm.6204

  日期：2012.5.30

  A method has been developed for the quantitation of isotopic labeling of proteins using liquid chromatography/tandem mass spectrometry (LC/MS/MS) for the application of protein nuclear magnetic resonance (NMR) studies. NMR relies on specific isotopic nuclei, such as 13C and 15N, for detection and, therefore, isotopic labeling is an important sample preparation step prior to in‐depth structural characterization

  已经开发出一种使用液相色谱/串联质谱法（LC / MS / MS）定量蛋白质同位素标记的方法，用于蛋白质核磁共振（NMR）研究。NMR依靠特定的同位素核（例如13 C和15 N）进行检测，因此，同位素标记是蛋白质深入结构表征之前的重要样品制备步骤。这项研究的目的是开发一种鲁棒的定量测定方法，以评估蛋白质中的同位素标记，同时保留有关单个氨基酸标记程度的信息。
• Three-Minute Enantioselective Amino Acid Analysis by Ultra-High-Performance Liquid Chromatography Drift Tube Ion Mobility-Mass Spectrometry Using a Chiral Core–Shell Tandem Column Approach
  作者：Simon Jonas Jaag、Younes Valadbeigi、Tim Causon、Harald Gross、Michael Lämmerhofer

  DOI：10.1021/acs.analchem.3c05426

  日期：2024.2.13

  Fast liquid chromatography (LC) amino acid enantiomer separation of 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) derivatives using a chiral core–shell particle tandem column with weak anion exchange and zwitterionic-type quinine carbamate selectors in less than 3 min was achieved. Enantiomers of all AQC-derivatized proteinogenic amino acids and some isomeric ones (24 in total plus achiral

  使用具有弱阴离子交换和两性离子型奎宁氨基甲酸酯选择器的手性核壳颗粒串联柱，在不到 3 分钟的时间内实现了 6-氨基喹啉基-N-羟基琥珀酰亚胺基氨基甲酸酯 (AQC) 衍生物的快速液相色谱 (LC) 氨基酸对映体分离。所有 AQC 衍生的蛋白氨基酸和一些异构体（总共 24 个加上非手性甘氨酸）的对映体均进行基线分离（ R s > 1.5，谷氨酸除外， R s = 1.3），而不同氨基酸和结构异构体的峰（相同构型的组成异构体和非对映异构体（亮氨酸和苏氨酸）有不同程度的重叠。因此，添加了漂移管离子淌度质谱仪（即 LC-IM-MS）作为额外的选择性过滤器，而无需延长运行时间。 IM 分离维度与高分辨率解复用相结合，能够确认苏氨酸异构体（苏氨酸、异位苏氨酸、高丝氨酸），而亮氨酸、异亮氨酸和异位异亮氨酸具有几乎相同的碰撞截面 ( DT CCS N2 ) 值并添加对部分 LC 分离没有选择性。密度泛函理论
• Measurement of 15N enrichment of glutamine and urea cycle amino acids derivatized with 6-aminoquinolyl-N-hydroxysuccinimidyl carbamate using liquid chromatography–tandem quadrupole mass spectrometry
  作者：Hidehiro Nakamura、Sachise Karakawa、Akiko Watanabe、Yasuko Kawamata、Tomomi Kuwahara、Kazutaka Shimbo、Ryosei Sakai

  DOI：10.1016/j.ab.2015.02.002

  日期：2015.5

  6-Aminoquinolyl-N-hydroxysuccinimidyl carbamate (AQC) is an amino acid-specific derivatizing reagent that has been used for sensitive amino acid quantification by liquid chromatography-tandem quadrupole mass spectrometry (LC-MS/MS). In this study, we aimed to evaluate the ability of this method to measure the isotopic enrichment of amino acids and to determine the positional N-15 enrichment of urea cycle amino acids (i.e., arginine, omithine, and citrulline) and glutamine. The distribution of the M and M + 1 isotopomers of each natural AQC-amino acid was nearly identical to the theoretical distribution. The standard deviation of the (M + 1)/M ratio for each amino acid in repeated measurements was approximately 0.1%, and the ratios were stable regardless of the injected amounts. Linearity in the measurements of N-15 enrichment was confirmed by measuring a series of N-15-labeled arginine standards. The positional N-15 enrichment of urea cycle amino acids and glutamine was estimated from the isotopic distribution of unique fragment ions generated at different collision energies. This method was able to identify their positional N-15 enrichment in the plasma of rats fed 15N-labeled glutamine. These results suggest the utility of LC-MS/MS detection of AQC-amino acids for the measurement of isotopic enrichment in N-15-labeled amino acids and indicate that this method is useful for the study of nitrogen metabolism in living organisms. (C) 2015 Elsevier Inc. All rights reserved.