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Comparison of the isomeric α-amino acyl adenylates and amino acid phosphoramidates of adenosine by electrospray ionization tandem mass spectrometry.
MedLine Citation:
PMID:  21192024     Owner:  NLM     Status:  In-Process    
Abstract/OtherAbstract:
The isomeric α-amino acyl adenylates and amino acid phosphoramidates of adenosine were synthesized and analyzed in detail by electrospray ionization tandem mass spectrometry (ESI-MS(n)). In ESI-MS/MS of α-amino acyl adenylates, the novel rearrangement ion [cAMP-H](-) observed as the most intense signal was formed through the pentacoordinate phosphorus intermediate with a six-membered ring by nucleophilic attack of the 3'-hydroxyl group on the phosphorus atom. In contrast, for the amino acid phosphoramidate of adenosine, the phosphorus atom could be attacked not only by the carboxylic group to form the cyclic aminoacyl phosphoramidates (CAPAs), but also by the nitrogen atom on the nucleobase leading to intramolecular phosphoryl group migration. It was found that the sodium ion having multidentate binding ability played an essential role in this characteristic rearrangement. The proposed mechanisms were supported by the MS/MS study, deuterium-labeled experiments, high-resolution tandem mass spectrometry and moderate calculations at the B3LYP/6-31G* level. The characteristic fragmentation patterns of α-amino acyl phosphates and amino acid phosphoramidates allows identification of stereoisomers when either the phosphorylation is at the N-terminus or C-terminus of amino acids.
Authors:
Xiang Gao; Zhiping Zeng; Pengxiang Xu; Guo Tang; Yan Liu; Yufen Zhao
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  25     ISSN:  1097-0231     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2011 Jan 
Date Detail:
Created Date:  2010-12-30     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  291-300     Citation Subset:  IM    
Copyright Information:
Copyright © 2010 John Wiley & Sons, Ltd.
Affiliation:
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, P.R. China.
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