2-(Quinolin-6-ylcarbamoylamino)acetic acid | 150331-55-8

• 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: 2-(Quinolin-6-ylcarbamoylamino)acetic acid
• CAS: 150331-55-8
• 化学式: C₁₂H₁₁N₃O₃
• mdl: MFCD17128346
• 分子量: 245.238
• InChiKey: DXEKOJIDPPOBDC-UHFFFAOYSA-N

物化性质

• 沸点：
  484.2±41.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  91.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 carboxypeptidase Y 作用下， 以 aq. buffer 为溶剂， 生成 2-(Quinolin-6-ylcarbamoylamino)acetic acid
  参考文献：
  名称：

  增强的羧肽酶功效和肽差向异构体的分化

  摘要：

  羧肽酶酶促切割肽内C-末端氨基酸的肽键。在人类中，它参与蛋白质和肽的酶促合成和成熟。羧肽酶 A 和 Y 难以水解二肽的肽键和一些其他氨基酸序列。对不同 N 阻断基团的早期研究得出结论，较大的部分增加了底物对用羧肽酶水解肽键的敏感性。该研究最终证明 6-氨基喹啉-N-羟基琥珀酰亚胺氨基甲酸酯 (AQC) 作为 N 封闭基团极大地增强了羧肽酶的底物水解。在氨基酸和肽的 N 末端添加 AQC 还可以通过质谱检测改善色谱峰形和灵敏度。在现代蛋白质组学出现之前，这些酶已用于氨基酸序列测定。然而，大多数现代蛋白质组学方法假定所有肽都由l-氨基酸，因此无法区分肽序列中的 L-和d-氨基酸。允许手性分化的大多数现有方法要么需要合成标准，要么在该过程中引起外消旋化。该研究强调了肽内d-氨基酸对羧肽酶 Y 酶水解的抗性。这种立体选择性在筛选低丰度肽差向异构体时可能是有利的。

  DOI：

  10.1016/j.ab.2021.114451

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。
• 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.
• AUTOMATED SAMPLING AND REACTION SYSTEM FOR HIGH PRESSURE LIQUID CHROMATOGRAPHY AND OTHER TYPES OF DETECTION
  申请人：Waters Technologies Corporation

  公开号：US20160195564A1

  公开（公告）日：2016-07-07

  Automated sampling and reaction systems and methods of using the same are provided. The automated sampling and reaction system has a microreactor in fluidic communication with an external sampling valve. The external sampling valve is connected to a priming valve and can be configured to draw sample from a reactor or a reactor stream. The microreactor is connected to a reagent valve and an injection valve. The reagent valve can be configured to draw reagent from a reagent reservoir and discharge reagent to the microreactor to react with sample. The priming valve can be configured to draw wash from a wash reservoir and discharge wash to the external sampling valve to move sample from the external sampling valve to the microreactor. The injection valve is in fluidic communication with a column or detector and discharges the secondary sample into a solvent composition stream.