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Reactivity of nitrogen atoms in adenine and (Ade)2Cu complexes towards ribose and 2-furanmethanol: Formation of adenosine and kinetin.
- Source :
-
Food chemistry [Food Chem] 2017 Jan 15; Vol. 215, pp. 463-9. Date of Electronic Publication: 2016 Aug 05. - Publication Year :
- 2017
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Abstract
- To explore the interaction of nucleosides and nucleobases in the context of the Maillard reaction and to identify the selectivity of purine nitrogen atoms towards various electrophiles, model systems composed of adenine or adenosine, glycine, ribose and/or 2-furanmethanol (with and without copper) were studied in aqueous solutions heated at 110°C for 2h and subsequently analyzed by ESI/qTOF/MS/MS in addition to isotope labelling techniques. The results indicated that ribose selectively formed mono-ribosylated N(6) adenine, but in the presence of (Ade)2Cu complex the reaction mixture generated mono-, di- and tri-substituted sugar complexes and their hydrolysis products of mono-ribosylated N(6) and N(9) adenine adducts and di-ribosylated N(6,9) adenine. Furthermore, the reaction of 2-furanmethanol with adenine in the presence of ribose generated kinetin and its isomer, while its reaction with adenosine generated kinetin riboside, as confirmed by comparing the MS/MS profiles of these adducts to those of commercial standards.<br /> (Copyright © 2016 Elsevier Ltd. All rights reserved.)
Details
- Language :
- English
- ISSN :
- 1873-7072
- Volume :
- 215
- Database :
- MEDLINE
- Journal :
- Food chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 27542499
- Full Text :
- https://doi.org/10.1016/j.foodchem.2016.08.012