Fragmentation study of tryptophan-derived metabolites induced by electrospray ionization mass spectrometry for highly sensitive analysis,Analyst

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Fragmentation study of tryptophan-derived metabolites induced by electrospray ionization mass spectrometry for highly sensitive analysis
Analyst ( IF 3.6 ) Pub Date : 2021-2-12 , DOI: 10.1039/d0an02069a
Daiki Asakawa _{1,

2,

3} , Hajime Mizuno _{3,

4,

5,

6} , Eiji Sugiyama _{3,

4,

5,

6} , Kenichiro Todoroki _{3,

4,

5,

6}

Affiliation

Liquid chromatography–tandem mass spectrometry (LC–MS/MS) is interfaced with electrospray ionization (ESI), which generally produces intact gas-phase ions of biomolecules. However, ESI induces the fragmentation of tryptophan-derived metabolites, which are known to act as neurotransmitters and psychoactive drugs. Tryptophan-derived metabolites undergo N–C_α bond dissociation during ESI, producing a fragment ion with a spiro[cyclopropane-indolium] backbone. Fragmentation is suppressed by the presence of an α-carboxyl group and the modification of amino groups. In particular, tryptamine and serotonin, which lack such functional groups, produce more intense fragment-ion signals than protonated molecules. The multiple reaction monitoring (MRM)-based quantitative analysis of tryptamine and serotonin used the fragment ions produced from in-source collision-induced dissociation as the precursor ions, which improved the signal-to-noise ratio of the resulting spectra. The present method allows for the quantitative analysis of tryptamine and serotonin with high sensitivity.

中文翻译：

电喷雾电离质谱法诱导的色氨酸衍生代谢物的碎片化研究，用于高灵敏度分析

液相色谱-串联质谱（LC-MS / MS）与电喷雾电离（ESI）相连，电喷雾电离通常可产生完整的生物分子气相离子。但是，ESI会诱导色氨酸衍生的代谢产物的碎裂，而后者被称为神经递质和精神活性药物。色氨酸衍生的代谢产物经历N– _CαESI过程中发生键解离，产生带有螺环丙烷-吲哚骨架的碎片离子。通过α-羧基的存在和氨基的修饰抑制断裂。尤其是缺乏这种官能团的色胺和5-羟色胺比质子化分子产生更强烈的碎片离子信号。基于多反应监测（MRM）的色胺和5-羟色胺定量分析将源内碰撞诱导的离解产生的碎片离子用作前体离子，从而提高了所得光谱的信噪比。本方法允许高灵敏度定量分析色胺和5-羟色胺。

更新日期：2021-02-23

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