[13C3,15N]-半胱氨酸-谷胱甘肽 | 1028814-07-4

• 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
• 中文名称: [13C3,15N]-半胱氨酸-谷胱甘肽
• 英文名称: [1,2,3-13C,15N]-Cys-glutathione
• 英文别名: glutathione；GSH；γ-glutamyl[¹³C₃,¹⁵N]cysteinylglycine；(2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-sulfanyl(1,2,3-13C3)propan-2-yl](15N)amino]-5-oxopentanoic acid
• CAS: 1028814-07-4
• 化学式: C₁₀H₁₇N₃O₆S
• 分子量: 311.288
• InChiKey: RWSXRVCMGQZWBV-GOVIAEJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.5
• 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：
  160
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [13C3,15N]-半胱氨酸-谷胱甘肽 在 过甲酸 作用下， 反应 2.5h， 生成 glutathionesulfonic acid
  参考文献：
  名称：

  Quantitation of glutathione and its oxidation products in erythrocytes by multiple-label stable-isotope dilution

  摘要：

  A multiple-label stable isotope dilution assay for quantifying glutathione (GSH), glutathione disulfide (GSSG), and glutathione sulfonic acid in erythrocytes was developed. As the internal standards, [C-13(3),N-15]glutathione, [C-13(4),N-15(2)]glutathione disulfide, and [C-13(3),N-15]glutathione sulfonic acid were used. Analytes and internal standards were detected by LC-MS/MS after derivatization of GSH with iodoacetic acid and dansylation of all compounds under study. The calibration functions for all analytes relative to their respective isotopologic standards revealed slopes close to 1.0 and negligible intercepts. As various labelings of the standards for GSH and GSSG were used, their simultaneous quantitation was possible, although GSH was partly oxidized to its disulfide during analysis. The degree of this artifact formation of GSSG was calculated from the abundance of the mixed disulfide formed from unlabeled GSH and its respective standard. Thus, the detected GSSG amount could be corrected for the artifact amount. In this way, the amount of GSSG in erythrocytes was found to be less than 0.5% of the GSH concentration. Similar to GSSG, the detected amount of glutathione sulfonic acid was found to be formed at least in part during the analytical process, but the degree could not be quantified. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2013.09.029
• 作为产物：
  描述：

  [1,2,3-13C,15N]N-Fmoc-Cys(S-trityl) 、 芴甲氧羰基-L-谷氨酸 1-叔丁酯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 [13C3,15N]-半胱氨酸-谷胱甘肽
  参考文献：
  名称：

  Facile preparation of leukotrienes C4, D4 and E4 containing carbon-13 and nitrogen-15 for quantification of cysteinyl leukotrienes by mass spectrometry

  摘要：

  近年来，利用液相色谱/电喷雾串联质谱联用技术可以在一次实验中快速分析生物样本中的多种类二十烷烃，因此需要用重同位素标记的类二十烷烃作为内标物，以便对类二十烷烃分析物进行定量分析。本研究介绍了一种在半胱氨酰残基中含有三个 13C 原子和一个 15N 原子的半胱氨酰白三烯（白三烯 C4、D4 和 E4）的实用制备方法。该方法包括固相肽合成，以制造半胱氨酰残基中含有重同位素的谷胱甘肽，并将该三肽与市售的白三烯 A4 甲酯反应，得到标记的白三烯 C4 甲酯，再将其水解为标记的白三烯 C4。标记白三烯 E4 的制备方法与使用标记半胱氨酸的方法相同。标记的白三烯 D4 是用市售的γ-谷氨酰转肽酶处理标记的白三烯 C4 制备的。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1414

文献信息

• Facile preparation of leukotrienes C4, D4 and E4 containing carbon-13 and nitrogen-15 for quantification of cysteinyl leukotrienes by mass spectrometry
  作者：Farideh Ghomashchi、James G. Bollinger、Michael H. Gelb

  DOI：10.1002/jlcr.1414

  日期：2007.7

  With the recent ability to use combined liquid chromatography/electrospray tandem mass spectrometry to analyze for several eicosanoids in biological samples in a single and rapid experiment, heavy isotope-labeled eicosanoids are needed as internal standards in order to quantify eicosanoid analytes. The present study describes a practical preparation of cysteinyl leukotrienes (leukotriene C4, D4 and E4) with three 13C atoms and one 15N atom in the cysteinyl residue. The method involves solid-phase peptide synthesis to make glutathione with heavy isotopes in the cysteinyl residue and reaction of this tripeptide with commercially available leukotriene A4 methyl ester to give labeled leukotriene C4 methyl ester, which is hydrolyzed to labeled leukotriene C4. Labeled leukotriene E4 is prepared in the same way with the use of labeled cysteine. Labeled leukotriene D4 is prepared by treatment of labeled leukotriene C4 with commercially available γ-glutamyl transpeptidase. Copyright © 2007 John Wiley & Sons, Ltd.

  近年来，利用液相色谱/电喷雾串联质谱联用技术可以在一次实验中快速分析生物样本中的多种类二十烷烃，因此需要用重同位素标记的类二十烷烃作为内标物，以便对类二十烷烃分析物进行定量分析。本研究介绍了一种在半胱氨酰残基中含有三个 13C 原子和一个 15N 原子的半胱氨酰白三烯（白三烯 C4、D4 和 E4）的实用制备方法。该方法包括固相肽合成，以制造半胱氨酰残基中含有重同位素的谷胱甘肽，并将该三肽与市售的白三烯 A4 甲酯反应，得到标记的白三烯 C4 甲酯，再将其水解为标记的白三烯 C4。标记白三烯 E4 的制备方法与使用标记半胱氨酸的方法相同。标记的白三烯 D4 是用市售的γ-谷氨酰转肽酶处理标记的白三烯 C4 制备的。Copyright © 2007 John Wiley & Sons, Ltd. All Rights Reserved.
• Quantitation of glutathione and its oxidation products in erythrocytes by multiple-label stable-isotope dilution
  作者：Julia Reinbold、Peter Koehler、Michael Rychlik

  DOI：10.1016/j.ab.2013.09.029

  日期：2014.1

  A multiple-label stable isotope dilution assay for quantifying glutathione (GSH), glutathione disulfide (GSSG), and glutathione sulfonic acid in erythrocytes was developed. As the internal standards, [C-13(3),N-15]glutathione, [C-13(4),N-15(2)]glutathione disulfide, and [C-13(3),N-15]glutathione sulfonic acid were used. Analytes and internal standards were detected by LC-MS/MS after derivatization of GSH with iodoacetic acid and dansylation of all compounds under study. The calibration functions for all analytes relative to their respective isotopologic standards revealed slopes close to 1.0 and negligible intercepts. As various labelings of the standards for GSH and GSSG were used, their simultaneous quantitation was possible, although GSH was partly oxidized to its disulfide during analysis. The degree of this artifact formation of GSSG was calculated from the abundance of the mixed disulfide formed from unlabeled GSH and its respective standard. Thus, the detected GSSG amount could be corrected for the artifact amount. In this way, the amount of GSSG in erythrocytes was found to be less than 0.5% of the GSH concentration. Similar to GSSG, the detected amount of glutathione sulfonic acid was found to be formed at least in part during the analytical process, but the degree could not be quantified. (C) 2013 Elsevier Inc. All rights reserved.