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Tricyclic nucleobase analogs and their ribosides as substrates and inhibitors of purine-nucleoside phosphorylases III. Aminopurine derivatives

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dc.abstract.enEtheno-derivatives of 2-aminopurine, 2-aminopurine riboside, and 7-deazaadenosine (tubercidine) were prepared and purified using standard methods. 2-Aminopurine reacted with aqueous chloroacetaldehyde to give two products, both exhibiting substrate activity towards bacterial (E. coli) purine-nucleoside phosphorylase (PNP) in the reverse (synthetic) pathway. The major product of the chemical synthesis, identified as 1,N2-etheno-2-aminopurine, reacted slowly, while the second, minor, but highly fluorescent product, reacted rapidly. NMR analysis allowed identification of the minor product as N2,3-etheno-2-aminopurine, and its ribosylation product as N2,3-etheno-2-aminopurine-N2--d-riboside. Ribosylation of 1,N2-etheno-2-aminopurine led to analogous N2--d-riboside of this base. Both enzymatically produced ribosides were readily phosphorolysed by bacterial PNP to the respective bases. The reaction of 2-aminopurine-N9- -d-riboside with chloroacetaldehyde gave one major product, clearly distinct from that obtained from the enzymatic synthesis, which was not a substrate for PNP. A tri-cyclic 7-deazaadenosine (tubercidine) derivative was prepared in an analogous way and shown to be an eective inhibitor of the E. coli, but not of the mammalian enzyme. Fluorescent complexes of amino-purine analogs with E. coli PNP were observed.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorStachelska-Wierzchowska, Alicja
dc.contributor.authorWierzchowski, Jacek
dc.contributor.authorBzowska, Maria
dc.contributor.authorStolarski, Ryszard
dc.contributor.authorWielgus-Kutrowska, Beata
dc.contributor.authorGórka, Michał
dc.date.accessioned2024-01-26T11:06:47Z
dc.date.available2024-01-26T11:06:47Z
dc.date.issued2020
dc.description.financeŚrodki finansowe, o których mowa w art. 365 pkt. 2 ustawy
dc.description.number3
dc.description.volume25
dc.identifier.doi10.3390/MOLECULES25030681
dc.identifier.issn1420-3049
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/123805
dc.languageeng
dc.pbn.affiliationphysical sciences
dc.relation.ispartofMolecules
dc.relation.pages1-19
dc.rightsClosedAccess
dc.sciencecloudnosend
dc.titleTricyclic nucleobase analogs and their ribosides as substrates and inhibitors of purine-nucleoside phosphorylases III. Aminopurine derivatives
dc.typeJournalArticle
dspace.entity.typePublication