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A novel rearrangement in electrospray ionization multistage tandem mass spectrometry of amino acid ester cyclohexyl phosphoramidates of AZT

✍ Scribed by Yi Chen; Yingwu Yin; Xiaobin Sun; Xiaohong Liu; Haiyan Wang; Yufen Zhao

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
141 KB
Volume
40
Category
Article
ISSN
1076-5174

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✦ Synopsis

Abstract

Several amino acid ester cyclohexyl phosphoramidates of AZT as anti‐HIV prodrugs were synthesized and investigated by electrospray ionization tandem mass spectrometry (ESI‐MS^n^). A novel methoxy group migration from the carbonyl group to the phosphoryl group was observed in ESI‐MS2. This migration is believed to be a general pathway for ions with a methyl ester moiety at the γ‐position to a phosphoric acid moiety, which is assisted with metal ions such as Li^+^, Na^+^ and K^+^. Coordination between metal ions with both the carbonyl oxygen and phosphoryl oxygen might be a key factor responsible for this migration. Copyright © 2005 John Wiley & Sons, Ltd.

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