A Facile and High-Sensitivity Method for Determining Proteinogenic Amino Acid Enantiomers by Integrating Chiral Phosphinate Derivatizing, 31P NMR and Parallel Reaction Monitoring,Analytical Chemistry

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A Facile and High-Sensitivity Method for Determining Proteinogenic Amino Acid Enantiomers by Integrating Chiral Phosphinate Derivatizing, 31P NMR and Parallel Reaction Monitoring
Analytical Chemistry ( IF 6.7 ) Pub Date : 2023-05-05 , DOI: 10.1021/acs.analchem.2c03432
Yoapoing Shi ₁ , Dipendu Mandal ₁ , Zhenbin Zhang ₁ , Yufen Zhao _{1,

2}

Affiliation

Here, we have documented a new protocol to determine d/l-amino acids by derivatizing amino acids via a chiral phosphinate. (R_P)-l-Menthyl phenylphosphinate was able to bond both primary and secondary amines, as well as improve the sensitivity of analytes in MS. Eighteen pairs of amino acids were successfully labeled except for Cys which has a thiol group on the side chain, and the chirality of amino acids can be discriminated by ³¹P NMR. Seventeen pairs of amino acids were separated by a C18 column within 45 min of elution, and resolution values ranged from 2.01 to 10.76. The lowest limit of detection was 10 pM acquired at parallel reaction monitoring, in which two factors collectively contributed that the ability of protonation of phosphine oxide and the sensitivity of parallel reaction monitoring. Chiral phosphine oxides might be a promising tool in future chiral metabolomics.

中文翻译：

一种通过整合手性次膦酸盐衍生化、31P NMR 和平行反应监测来测定蛋白质氨基酸对映体的简便且高灵敏度的方法

在这里，我们记录了一个新的协议，通过手性次膦酸盐衍生化氨基酸来确定d / l-氨基酸。( R _P )- l -苯基次膦酸薄荷酯能够键合伯胺和仲胺，并提高 MS 中分析物的灵敏度。除侧链带有巯基的Cys外，共成功标记了18对氨基酸，氨基酸的手性可通过³¹P核磁共振。在洗脱后 45 分钟内，17 对氨基酸被 C18 柱分离，分辨率值范围为 2.01 至 10.76。平行反应监测的最低检测限为10 pM，其中氧化膦的质子化能力和平行反应监测的灵敏度两个因素共同作用。手性氧化膦可能是未来手性代谢组学中有前途的工具。

更新日期：2023-05-05

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