Development of derivatization reagents bearing chiral 4-imidazolidinone for distinguishing primary amines from other amino acids and application to the liquid chromatography-tandem mass spectrometric analysis of miso
Development of derivatization reagents bearing chiral 4-imidazolidinone for distinguishing primary amines from other amino acids and application to the liquid chromatography-tandem mass spectrometric analysis of miso
复制标题
DOI：
10.1016/j.chroma.2021.462341
复制
发表时间：
2021-06-27
影响因子：
4.1
通讯作者：
Fukushima, Takeshi
中科院分区：
文献类型：
--
作者：
Sakamoto, Tatsuya;Onozato, Mayu;Fukushima, Takeshi
我们设计并合成了三种带有手性4 - 咪唑烷酮的新型衍生试剂，即2 - (3 - ((苄氧基)羰基) - 1 - 甲基、乙基和 - 苯基 - 5 - 氧代咪唑烷 - 4 - 基)乙酸琥珀酰亚胺酯（CIMs），用于液相色谱 - 串联质谱（LC - MS/MS）分析。CIMs能够根据其在MS/MS中独特的前体离子m/z降低以形成产物离子的特性，将伯胺与其他化合物（如仲胺和酚类）区分开来。作为氨基酸衍生试剂，对CIMs在氨基酸对映体分离和检测灵敏度方面进行了比较。带有1 - 甲基 - 5 - 氧代咪唑烷酮部分的CIMa - OSu在CIM试剂中具有最佳的光学分辨率和检测灵敏度。接下来，我们应用（R） - CIMa - OSu通过液相色谱 - 三重四极杆质谱测定味噌中的氨基酸。所提出的方法能够高灵敏度地同时测定样品中的20种L - 氨基酸和两种D - 氨基酸（D - 丙氨酸和D - serine）（检测限为5 - 238 fmol，信噪比为3.3）。用CIMa - OSu衍生后，通过使用高分辨率轨道阱质谱仪，可以确定色谱图中的每个峰是否为伯胺成分。（C）2021爱思唯尔有限公司。保留所有权利。
We designed and synthesized three novel derivatization reagents bearing chiral 4-imidazolidinone, namely succinimidyl 2-(3-((benzyloxy)carbonyl)-1-methyl, ethyl, and -phenyl-5-oxoimidazolidin-4-yl)acetates (CIMs), for use in liquid chromatography-tandem mass spectrometry (LC-MS/MS) analysis. The CIMs were able to discriminate primary amines from other compounds such as secondary amines and phenols, based on their unique m/z reduction of precursor ion to form product ion in MS/MS. As amino acid derivatization reagents, the CIMs were compared in terms of enantioseparation of amino acid and detection sensitivity. CIMa-OSu with 1-methyl-5-oxoimidazolidinone moiety gave the best optical resolution and detection sensitivity among the CIM reagents. Next, we applied (R)-CIMa-OSu to determine amino acids in miso by LC-triple-quadrupole MS. The proposed method achieved simultaneous determination of 20 L-amino acids and two D-amino acids (D-alanine and D-serine) in the sample with a high sensitivity (limits of detection 5-238 fmol, signal-to-noise ratio 3.3). After derivatization with CIMa-OSu, it was possible to determine whether each peak in the chromatogram was a component of primary amine or not, by using a high-resolution orbitrap MS instrument. (C) 2021 Elsevier B.V. All rights reserved.