A Pyridinium Derivatization Reagent for Highly Sensitive Detection of Poly(carboxylic acid)s Using Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry,ACS Environmental Au

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A Pyridinium Derivatization Reagent for Highly Sensitive Detection of Poly(carboxylic acid)s Using Liquid Chromatography-Electrospray Ionization-Tandem Mass Spectrometry
ACS Environmental Au ( IF 6.7 ) Pub Date : 2022-06-28 , DOI: 10.1021/jasms.2c00086
Shimba Kawasue ₁ , Yohei Sakaguchi ₁ , Reiko Koga ₁ , Hideyuki Yoshida ₁ , Hitoshi Nohta ₁

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Short-chain fatty acids are difficult to analyze with high sensitivity using liquid chromatography-electrospray ionization-mass spectrometry (LC-ESI-MS) owing to the high polarity of their carboxyl groups. Various derivatization methods have been developed; however, most are effective only for monocarboxylic acids and not for those having multiple carboxyl groups. Therefore, we successfully attempted to synthesize a derivatization reagent that could analyze both mono- and poly(carboxylic acid)s with high sensitivity. We optimized our derivatization reagent by modifying the structure of the reaction site, hydrophobicity of the derivatized compound, and linker structure connecting the reaction site to the permanently charged substructure. The reactivity toward carboxyl groups was improved by employing a piperidine moiety as the reaction site, and the ESI efficiency was improved by the highly hydrophobic and permanently charged triphenylpyridinium group. Furthermore, the incorporation of an alkyl linker enabled polylabeling. When the optimized reagent was applied to mono-, di-, tri-, and tetracarboxylic acids, the ESI efficiency increased with polylabeling; thus, our derivatization reagent outperforms existing derivatization methods and enables the analysis of poly(carboxylic acid)s with high sensitivity. Since this derivatization reagent can be applied to most carboxyl-containing compounds, it can be widely used for lipidomics, proteomics, and metabolomics.

中文翻译：

使用液相色谱-电喷雾电离-串联质谱法对聚羧酸进行高灵敏度检测的吡啶鎓衍生试剂

由于其羧基的高极性，短链脂肪酸难以使用液相色谱-电喷雾电离-质谱 (LC-ESI-MS) 进行高灵敏度分析。已经开发了各种衍生化方法；然而，大多数仅对一元羧酸有效，而对具有多个羧基的那些无效。因此，我们成功地尝试合成一种衍生化试剂，该试剂可以以高灵敏度分析单和聚（羧酸）。我们通过修改反应位点的结构、衍生化合物的疏水性以及将反应位点连接到永久带电子结构的接头结构来优化我们的衍生化试剂。通过使用哌啶部分作为反应位点，提高了对羧基的反应性，高疏水性和永久带电的三苯基吡啶鎓基团提高了 ESI 效率。此外，烷基接头的加入使多标记成为可能。当优化的试剂应用于单、二、三和四羧酸时，ESI 效率随着多标记而增加；因此，我们的衍生化试剂优于现有的衍生化方法，并且能够以高灵敏度分析聚（羧酸）。由于该衍生试剂可应用于大多数含羧基化合物，因此可广泛用于脂质组学、蛋白质组学和代谢组学。三羧酸和四羧酸，ESI 效率随着多标记而增加；因此，我们的衍生化试剂优于现有的衍生化方法，并且能够以高灵敏度分析聚（羧酸）。由于该衍生试剂可应用于大多数含羧基化合物，因此可广泛用于脂质组学、蛋白质组学和代谢组学。三羧酸和四羧酸，ESI 效率随着多标记而增加；因此，我们的衍生化试剂优于现有的衍生化方法，并且能够以高灵敏度分析聚（羧酸）。由于该衍生试剂可应用于大多数含羧基化合物，因此可广泛用于脂质组学、蛋白质组学和代谢组学。

更新日期：2022-06-28

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