gamma-Glutamyl-seryl-glycine | 38837-74-0

• 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: gamma-Glutamyl-seryl-glycine
• 英文别名: γ-glutamyl-seryl-glycine；γ-Glu-Ser-Gly；γ-L-glutamyl-L-serylglycine；(2S)-2-amino-5-[[(2S)-1-(carboxymethylamino)-3-hydroxy-1-oxopropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 38837-74-0
• 化学式: C₁₀H₁₇N₃O₇
• 分子量: 291.261
• InChiKey: XKAHUJADEPXYAH-WDSKDSINSA-N

物化性质

• 沸点：
  808.4±65.0 °C(Predicted)
• 密度：
  1.481±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.5
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  179
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  gamma-Glutamyl-seryl-glycine 、 4-(2-(ethoxymethylene)-3-oxobutanamido)-N,N,N-trimethylbenzeneaminium iodide 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  化学同位素标记辅助液相色谱-质谱法能够灵敏、准确地测定复杂生物样品中的二肽和三肽

  摘要：

  小肽因其独特的特性和多样化的生物学功能而受到越来越多的关注。然而，由于其丰度低且存在多种结构异构体，实现快速分离和准确定量仍然是一个挑战。在这项研究中，我们开发了一种使用同位素化学标记超灵敏测定生物样品中二肽/三肽的新方法。我们成功合成了一种新型衍生化试剂4-(2-(乙氧基亚甲基)-3-氧代丁酰胺基)-三甲基苯胺碘化物(EOTMBA)及其氘标记同位素试剂(-EOTMBA)。总共97个小肽，包括89个二肽和8个三肽，在60℃下1.5小时内可以在​​甲醇中完全衍生化。 EOTMBA 标记后，通过 LC-MS/MS 分析在 22 分钟内完成对这些二肽/三肽的分析。该方法的准确度为 86.3%–113%，定量限范围为 0.25 fmol/L 至 5 nmol/L。利用该方法，我们对取自健康个体和胆道疾病患者的 147 份血浆、49 份尿液和 46 份胆汁样本中的二肽/三肽进行了超灵敏和准确的定量。

  DOI：

  10.1016/j.cclet.2024.109670
• 作为产物：
  描述：

  L-Ser-Gly 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 氢气 、 三氟乙酸 作用下， 以 水 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 86.0h， 生成 gamma-Glutamyl-seryl-glycine
  参考文献：
  名称：

  Lo, Theodore W. C.; Thornalley, Paul J., Journal of the Chemical Society. Perkin transactions I, 1992, # 5, p. 639 - 643

  摘要：

  DOI：

文献信息

• Design of potent inhibitors for Schistosoma japonica glutathione S-transferase
  作者：Shu-Chuan Jao、Jessica Chen、Kelvin Yang、Wen-Shan Li

  DOI：10.1016/j.bmc.2005.07.077

  日期：2006.1

  We implemented both structure-based drug design and the concept of polyvalency to discover a series of potent and unsymmetrical Schistosoma japonicum glutathione S-transferase (SjGST) inhibitors 10-12. This strategy achieved not only an excellent enhancement (10- to 490-fold) in the inhibitory potency, compared to the monofunctional analogues 1-5, but was also an effective modification by selecting a hydrophobic moiety with a flexible linker. The designed compounds with a low micromolar hit demonstrate special values in refining the new generation of SjGST inhibitors. The stoichiometry of the binding is one inhibitor molecule per SjGST monomer via isothermal titration calorimetric measurement. (c) 2005 Elsevier Ltd. All rights reserved.
• Quantitative analysis of γ-glutamylpeptides by liquid chromatography-mass spectrometry and application for γ-glutamyltransferase assays
  作者：Sho Kobayashi、Yoshinori Tokairin、Takeru Miyakoshi、Takuya Saito、Keita Nagaoka、Yoshitaka Ikeda、Junichi Fujii、Hiroyuki Konno

  DOI：10.1016/j.ab.2019.04.023

  日期：2019.8

  gamma-Glutamylpeptides are largely produced via the action of gamma-glutamylcysteine synthetase or gamma-glutamyltransferase (GGT). GGT transfers the gamma-glutamyl moiety from glutathione (GSH) and other gamma-glutamyl compounds to amino acids, peptides, or water. A conventional GGT assay employs a synthetic donor substrate, which facilitates monitoring cleavage activity by means of colorimetric analyses but provides no information on the resulting gamma-glutamylpeptides. In this study, we report on the use of liquid chromatography-mass spectrometry (LC-MS) to quantitatively measure the levels of 21 gamma-glutamylpeptides including GSH and 45 amino acids, including Cys. Authentic compounds consisting of 17 chemically synthesized and commercially available 4 gamma-glutamylpeptides were adopted as references. We applied this method to the characterization of gamma-glutamylpeptides in blood plasma and livers of mice that had been treated with an overdose of acetaminophen. The established LC-MS-based assay was found to be useful for characterizing the gamma-glutamylation reaction under in vivo and in vitro conditions and was clearly helpful for understanding the physiological significance of the production of gamma-glutamylpeptides.