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Issue 6, 2004
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New nucleoside analogs from 2-amino-9-(β-d-ribofuranosyl)purine

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Abstract

Four novel derivatives of 2-amino-9-(β-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-(β-D-ribofuranosyl)-imidazo-[1,2a]purine (2), 3-(β-D-ribofuranosyl)-5-methylimidazo-[1,2a]purine (3), 3-(β-D-ribofuranosyl)-5-formylimidazo-[1,2a]purine (4) and 9-(β-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.

Graphical abstract: New nucleoside analogs from 2-amino-9-(β-d-ribofuranosyl)purine

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Publication details

The article was received on 16 Dec 2003, accepted on 06 Feb 2004 and first published on 25 Feb 2004


Article type: Paper
DOI: 10.1039/B316413F
Org. Biomol. Chem., 2004,2, 821-827

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

    P. Virta, T. Holmström, M. U. Roslund, P. Mattjus, L. Kronberg and R. Sjöholm, Org. Biomol. Chem., 2004, 2, 821
    DOI: 10.1039/B316413F

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