New Pyrimidine Cyclonucleosides with Hydrogenated Aglycones: Synthesis and X-Ray Structures |
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| Authors: | Anatoly D Shutalev Valeriy E Zavodnik Galina V Gurskaya |
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| Institution: | 1. Department of Organic Chemistry , State Academy of Fine Chemical Technology , Vernadsky Avenue 86, Moscow , 117571 , Russia;2. Karpov Institute of Physical Chemistry , Vorontsovo Pole 10, Moscow , 103064 , Russia;3. Engelhardt Institute of Molecular Biology, Acad. Sci. Russia , Vavilov Street 32, Moscow , 117984 , Russia |
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| Abstract: | Abstract Acid catalysed transformations of (6S)-6,5′-anhydro-6-hydroxy-1-(2′,3′-O-isopropylidene-β-D-ribofuranosyl)hexahydropyrimidine-2-thione are studied. (6R)-6,2′-anhydro-6-hydroxy-1-(α-D-ribofuranosyl)hexahydropyrimidine-2-thione was formed as a thermodynamically stable product. Two intermediates, (6S)-6,5′-anhydro-6-hydroxy-1-(β-D-ribofuranosyl)hexahydropyrimidine-2-thione and 6-hydroxy-1-(D-ribosyl)hexahydropyrimidine-2-thione and products of cleavage of glycosidic bond were identified in the reaction mixtures. Results of X-ray structural determination of the synthesised nucleosides are presented. |
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| Keywords: | Oxidative DNA lesion Thymine glycol Oligodeoxyribonucleotide Chemical synthesis Protecting groups |
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