Preparation of imidazolidinone compounds as derivatization reagent for diastereomerization and chromatographic separation of chiral organic acids
Preparation of imidazolidinone compounds as derivatization reagent for diastereomerization and chromatographic separation of chiral organic acids
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DOI：
10.1016/j.chroma.2022.463159
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发表时间：
2022-06-06
影响因子：
4.1
通讯作者：
Fukushima, Takeshi
中科院分区：
文献类型：
--
作者：
Umino, Maho;Sakamoto, Tatsuya;Fukushima, Takeshi
合成了一种可与羧基反应的5-（2-氨基乙基）-3-甲基-4-氧咪唑烷-1-羧酸苄基（cm -c -2- nh2）手性衍生化试剂，用于LC-MS/MS检测。手性和非手性有机酸，如乳酸、2-羟基丁酸、3-羟基丁酸、乙酸、琥珀酸、酒石酸、苹果酸和柠檬酸，均用CIM-C-2-NH2衍生；采用LC-MS/MS对其衍生物进行分析。我们研究了手性有机酸在十八烷基硅柱上的对映分离，除苹果酸外，在H2O-CH3CN流动相下的拆分值在1.31-2.19之间。与此相反，当使用比CIMC2-NH2含亚甲基少的5-（氨基甲基）3-甲基-4-氧咪唑烷-1-羧酸苄基（CIM-C-1-NH2）时，没有观察到手性有机酸的对映体分离。另外，苹果酸、酒石酸和琥珀酸具有两个羧基，质谱显示产物离子为m/z 278，而其他有机酸的质谱显示产物离子为m/z 91，对应于苯基部分。将该方法应用于商品葡萄酒中有机酸的分析，成功地检测出d、l乳酸等有机酸。(C) 2022 Elsevier B.V.版权所有
A chiral derivatization reagent for application in LC-tandem mass spectrometry (LC-MS/MS)-based detection, benzyl 5-(2-aminoethyl)-3-methyl-4-oxoimidazolidine-1-carboxylate (CIM-C-2-NH2), which can react with the carboxyl group, was synthesized. Both chiral and non-chiral organic acids such as lactic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, acetic acid, succinic acid, tartaric acid, malic acid, and citramalic acid were derivatized with CIM-C-2-NH2; their derivatives were analyzed by LC-MS/MS. We investigated the enantioseparation of chiral organic acids on an octadecylsilica column and obtained the resolution values within 1.31-2.19 with a mobile phase of H2O-CH3CN with the exception of malic acid. In contrast, no enantioseparation of the chiral organic acids was observed when benzyl 5-(aminomethyl)3-methyl-4-oxoimidazolidine-1-carboxylate (CIM-C-1-NH2), which bears fewer methylene units than CIMC2-NH2, was used. In addition, the mass spectra of malic acid, tartaric acid, and succinic acid, which have two carboxyl groups, showed product ions of m/z 278, while those of other organic acids showed product ions of m/z 91, corresponding to the benzyl moiety. The proposed method was applied to analyze organic acids in commercial wine, and some organic acids such as d -and L-lactic acid were successfully detected. (C) 2022 Elsevier B.V. All rights reserved.