Document Detail

Cytosine to uracil conversion through hydrolytic deamination of cytidine monophosphate hydroxy-alkylated on the amino group: a liquid chromatography - electrospray ionization - mass spectrometry investigation.
MedLine Citation:
PMID:  23019171     Owner:  NLM     Status:  In-Data-Review    
A novel pathway for cytosine to uracil conversion performed in a micellar environment, leading to the generation of uridine monophosphate (UMP), was evidenced during the alkylation reaction of cytidine monophosphate (CMP) by dodecyl epoxide. Liquid chromatography-electrospray ionization - ion trap - mass spectrometry was used to separate and identify the reaction products and to follow their formation over time. The detection of hydroxy-amino-dodecane, concurrently with free UMP, in the reaction mixture suggested that, among the various alkyl-derivatives formed, CMP alkylated on the amino group of cytosine could undergo tautomerization to an imine and hydrolytic deamination, generating UMP. Interestingly, no evidence for this peculiar conversion pathway was obtained when guanosine monophosphate (GMP), the complementary ribonucleotide of CMP, was also present in the reaction mixture, due to the fact that NH(2) -alkylated CMP was not formed in this case. The last finding emphasized the role played by CMP-GMP molecular interactions, mediated by a micellar environment, in hindering the alkylation reaction at the level of the cytosine amino group. Copyright © 2012 John Wiley & Sons, Ltd.
I Losito; R Angelico; B Introna; A Ceglie; F Palmisano
Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Journal of mass spectrometry : JMS     Volume:  47     ISSN:  1096-9888     ISO Abbreviation:  J Mass Spectrom     Publication Date:  2012 Oct 
Date Detail:
Created Date:  2012-09-28     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9504818     Medline TA:  J Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  1384-93     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 John Wiley & Sons, Ltd.
Dipartimento di Chimica, Università degli Studi di Bari "Aldo Moro", Via E. Orabona 4, 70126, Bari, Italy; Centro Interdipartimentale SMART, Università degli Studi di Bari "Aldo Moro", Via E. Orabona 4, 70126, Bari, Italy.
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