A novel methyl migration to the phosphoryl group with the formation of cyclic aminoacylphosphoramidates in electrospray ionization tandem mass spectra of amino acid ester phosphoramidates of antiviral nucleosides

被引：11
作者：
Gao, Xiang [1 ,2 ]
Zhu, Gangtian [1 ,2 ]
Zeng, Zhiping [1 ,2 ]
Chen, Weizhu [3 ]
Lin, Zhiwei [1 ,2 ]
Liu, Yan [1 ,2 ]
Xu, Pengxiang [1 ,2 ]
Zhao, Yufen [1 ,2 ,4 ]
机构：
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[2] Xiamen Univ, Key Lab Chem Biol Fujian Prov, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
[3] State Ocean Adm, Inst Oceanog 3, Xiamen 361005, Peoples R China
[4] Tsinghua Univ, Sch Sci, Key Lab Bioorgan Phosphorus Chem & Chem Biol, Dept Chem,Minist Educ, Beijing 100084, Peoples R China
来源：
RAPID COMMUNICATIONS IN MASS SPECTROMETRY | 2011年 / 25卷 / 08期
基金：
中国国家自然科学基金;
关键词：
ANTI-HIV EFFICACY; GAS-PHASE FRAGMENTATION; P-O; SPECTROMETRY; DERIVATIVES; D4T; REARRANGEMENT; DISSOCIATION; TECHNOLOGY; METABOLISM;
D O I：
10.1002/rcm.4955
中图分类号：
Q5 [生物化学];
学科分类号：
071010 ; 081704 ;
摘要：
The mass spectral behavior of amino acid methyl ester phosphoramidate derivatives have been investigated using electrospray ionization multistage mass spectrometry (ESI-MSn) and moderate theoretical calculations at the B3LYP/6-31G(d) level. A novel methyl group migration to the phosphoryl group with the formation of the intermediate cyclic aminoacylphosphoramidate was found. 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 the metal ion coordination with the phosphoryl and carbonyl groups and the intrinsic properties of phosphoryl group might be the key factors responsible for this novel migration. Copyright (C) 2011 John Wiley & Sons, Ltd.
引用
收藏
页码：1061 / 1069
页数：9
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