New nucleoside analogs from 2-amino-9-(β-D-ribofuranosyl)purine

P Virta, T Holmström, MU Roslund, Peter Mattjus, Leif Kronberg, R Sjöholm

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    Four novel derivatives of 2-amino-9-(beta-D-ribofuranosyl) purine ( 1) were synthesised and fully characterised. When 1 was reacted with chloroacetaldehyde (a), 2-chloropropanal (b), bromomalonaldehyde (c) and a mixture of chloroacetaldehyde + malonaldehyde (d), 3-(beta-D-ribofuranosyl)- imidazo-[1,2a] purine (2), 3-(beta-D-ribofuranosyl)-5- methylimidazo-[1,2a] purine (3), 3-(beta-D-ribofuranosyl)-5-formylimidazo-[1,2a] purine (4) and 9-(beta-D-ribofuranosyl)-2-( 3,5-diformyl-4-methyl-1,4-dihydro-1-pyridyl) purine (5) were formed, respectively. The products were isolated, purified by chromatography and characterised by MS, complete NMR assignment as well as fluorescence and UV spectroscopy. The yields of these reactions were moderate ( 14 - 20%). The fluorescence properties differed from those of the starting compound and the quantum yields were considerably lower.
    Original languageUndefined/Unknown
    Pages (from-to)821–827
    Number of pages7
    JournalOrganic and Biomolecular Chemistry
    Issue number6
    Publication statusPublished - 2004
    MoE publication typeA1 Journal article-refereed

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