Identification of amino acid phosphorodiamidates of antiviral nucleosides using electrospray ionisation tandem mass spectrometry

Cui J.; Gao X.; Fan A.; Zhang S.; Liu Y.; Xu P.; Zhao Y.

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Identification of amino acid phosphorodiamidates of antiviral nucleosides using electrospray ionisation tandem mass spectrometry

机译：使用电喷雾电离串联质谱法鉴定抗病毒核苷的氨基酸二氨基磷酸氨基磷酸酯

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Several amino acid phosphorodiamidate derivatives of d4T as anti-HIV prodrugs were synthesised and investigated using electrospray ionisation multistage tandem mass spectrometry (ESI-MSn). A novel methyl group migration in the gas phase was observed in ESI-MS2 of the sodium adducts of amino acid methyl ester of phosphorodiamidates of 2′,3′-didehydro- 2′,3′-dideoxythymidine (d4T). The proposed structures of the rearrangement ions were confirmed by high-resolution tandem mass spectrometry. A possible mechanism involving the pentacoordinate phosphoric-carboxylic phosphate anhydride was proposed, in which a seven-membered ring intermediate was formed by coordination with the metal ion between the phosphoryl group and carbonyl oxygen atom. Thus, the intrinsic properties of phosphoryl group might be the key factors responsible for this migration.

机译：合成并使用电喷雾电离多级串联质谱（ESI-MSn）研究了d4T的几种氨基酸二氨基磷酸二氨基酯衍生物，作为抗HIV前药。在ESI-MS2中，在2'，3'-二氢-2'，3'-二脱氧胸苷（d4T）的磷酸二氨基甲酸酯的氨基酸甲酯的钠加合物的ESI-MS2中观察到气相中新的甲基迁移。提出的重排离子结构已通过高分辨率串联质谱法得以证实。提出了一种可能的机制，涉及五配位的磷酸-羧基磷酸酐，其中通过与磷酰基和羰基氧原子之间的金属离子配位形成七元环中间体。因此，磷酰基的固有性质可能是造成这种迁移的关键因素。

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《European journal of mass spectrometry》 |2011年第2期|共9页
作者
Cui J.; Gao X.; Fan A.; Zhang S.; Liu Y.; Xu P.; Zhao Y.;
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正文语种 eng
中图分类质谱分析;
关键词
Amino acids; ESI-MS/MS; Methyl migration; Phosphorodiamidates;

机译：氨基酸;ESI-MS / MS;甲基迁移;磷酸二酰胺;

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专利

1. Identification of amino acid phosphorodiamidates of antiviral nucleosides using electrospray ionisation tandem mass spectrometry [J] . Cui J., Gao X., Fan A., European journal of mass spectrometry . 2011,第2期

机译：使用电喷雾电离串联质谱法鉴定抗病毒核苷的氨基酸二氨基磷酸氨基磷酸酯
2. A novel approach for identification and measurement of hemoglobin adducts with 1,2,3,4-diepoxybutane by liquid chromatography/electrospray ionisation mass spectrometry and matrix-assisted laser desorption/ionisation tandem mass spectrometry [J] . Basile A., Pocsfalvi G., Mamone G., Rapid Communications in Mass Spectrometry: RCM . 2001,第8期

机译：液相色谱/电喷雾电离质谱和基质辅助激光解吸/电离串联质谱法鉴定和测量1,2,3,4-二环氧丁烷的血红蛋白加合物的新方法
3. Identification of the 'wrong' active pharmaceutical ingredient in a counterfeit Halfan (TM) drug product using accurate mass electrospray ionisation mass spectrometry, accurate mass tandem mass spectrometry and liquid chromatography/mass spectrometry [J] . Wolff JC., Thomson LA., Eckers C. Rapid Communications in Mass Spectrometry: RCM . 2003,第3期

机译：使用准确的电喷雾质谱，准确的串联质谱和液相色谱/质谱法鉴定假冒的Halfan（TM）药品中的“错误”活性药物成分
4. Identification of isomeric mono-methylated nucleosides in ribonucleic acids by liquid chromatography - highly accurate tandem mass spectrometry [C] . Hiroshi Nakayama, Yoshio Yamauchi, Masato Taoka, ASMS Conference on Mass Spectrometry and Allied Topics . 2016

机译：通过液相色谱法鉴定核糖核酸中的异构单甲基化核苷 - 高精度串联质谱法
5. Chiral analysis of 19 common amino acids with electrospray ionisation mass spectrometry. [D] . Yao, Zhongping. 2000

机译：使用电喷雾电离质谱对19种常见氨基酸进行手性分析。
6. Electrospray ionisation-cleavable tandem nucleic acid mass tag–peptide nucleic acid conjugates: synthesis and applications to quantitative genomic analysis using electrospray ionisation-MS/MS [O] . Andrew Thompson, Mark Prescott, Noorhan Chelebi, 2007

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7. Electrospray mass and tandem mass spectrometry identification of ozone oxidation products of amino acids and small peptides [O] . Kotiaho Tapio, Eberlin Marcos N, Vainiotalo Pirjo, 2000

机译：电喷雾质谱和串联质谱鉴定氨基酸和小肽的臭氧氧化产物

Identification of amino acid phosphorodiamidates of antiviral nucleosides using electrospray ionisation tandem mass spectrometry

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