Document Detail

Identification of amino acid phosphorodiamidates of antiviral nucleoside using electrospray ionization tandem mass spectrometry.
MedLine Citation:
PMID:  21719918     Owner:  NLM     Status:  In-Data-Review    
Several amino acid phosphorodiamidate derivatives of d4T as anti-HIV prodrugs were synthesized and investigated using electrospray ionization multistage tandem mass spectrometry (ESI-MS(n)). A novel methyl group migration in gas phase was observed in ESI-MS(2) 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.
Juntao Cui; Xiang Gao; Aiting Fan; Shuangyan Zhang; Yan Liu; Pengziang Xu; Yufen Zhao
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  European journal of mass spectrometry (Chichester, England)     Volume:  17     ISSN:  1469-0667     ISO Abbreviation:  Eur J Mass Spectrom (Chichester, Eng)     Publication Date:  2011  
Date Detail:
Created Date:  2011-07-01     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101124748     Medline TA:  Eur J Mass Spectrom (Chichester, Eng)     Country:  England    
Other Details:
Languages:  eng     Pagination:  187-95     Citation Subset:  IM    
Department of Chemistry and The Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, PR China.
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