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首页> 外文期刊>Journal of mass spectrometry: JMS >Formation of cyclic acylphosphoramidates in mass spectra of N-monoalkyloxyphosphoryl amino acids using electrospray ionization tandemmass spectrometry
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Formation of cyclic acylphosphoramidates in mass spectra of N-monoalkyloxyphosphoryl amino acids using electrospray ionization tandemmass spectrometry

机译：使用电喷雾电离tandemmass光谱法在N-单烷氧基磷酰基氨基酸的质谱图中形成环状酰基磷酰胺盐

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摘要

The fragmentation reactions of N-monoalkyloxyphosphoryl amino acids (N-MAP-AAs) were studied by electrospray ionization tandem mass spectrometry (ESI-MS). The sodiated cyclic acylphosphoramidates (CAPAs) were formed through a characteristic pentacoordinate phosphate participated rearrangement reaction in the positive-ion ESI-MS/MS and HR-MS/MS of N-MAPAAs, in which the fragmentation patterns were clearly different from those observed in the corresponding ESI-MS/MS of N-dialkyloxyphosphoryl amino acids/peptides and N-phosphono amino acids. The formation of CAPAs depended on the chemical structures of N-terminal phosphoryl groups, such as alkyloxy group, negative charge and alkali metal ion. A possible integrated rearrangementmechanism for both P-N to P-O phosphoryl groupmigration and formation of CAPAs was proposed. The fragmentation patterns of CAPAs as novel intermediates in gas phase were also investigated. In addition, it was found that the formation of α-amino acid CAPAs was more favorable than β- or γ -CAPAs in gas phase, which was consistent with previous solution-phase experiments.
机译：通过电喷雾电离串联质谱（ESI-MS）研究了N-单烷氧基磷酰基氨基酸（N-MAP-AAs）的片段化反应。在N-MAPAAs的正离子ESI-MS / MS和HR-MS / MS中，特征性的五配位磷酸盐参与的重排反应是通过特征性的五配位磷酸盐参与的重排反应形成的。 N-二烷氧基磷酰基氨基酸/肽和N-膦酰基氨基酸的相应ESI-MS / MS。 CAPA的形成取决于N末端磷酰基的化学结构，例如烷氧基，负电荷和碱金属离子。提出了一种可能的整合重排机制，用于P-N向P-O磷酸基团的迁移和CAPA的形成。还研究了CAPAs作为新型气相中间体的裂解模式。另外，发现气相中α-氨基酸CAPA的形成比β-或γ-CAPAs更有利，这与先前的溶液相实验一致。

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