On the prebiotic synthesis of ribonucleotides: Photoanomerisation of cytosine nucleosides and nucleotides revisited

Matthew W. Powner, Carole Anastasi, Michael A. Crowe, Alastair L. Parkes, Jim Raftery, John D. Sutherland

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Recent work has emphasised the importance of D-ribose amino-oxazoline 1 in the synthesis of cytidine ribonucleosides under potentially prebiotic conditions. Upon treatment with cyanoacetylene, 1 is transformed into α-D-cytidine (α-2), and if an efficient means of anomerising this nucleoside or a derivative thereof were to be found, then the synthesis of one of the key β-D-nucleosides required to make RNA would be realised. Photoanomerisation of α-2 has previously been described, but the yield was extremely low. Therefore, the present study was initiated to determine whether this low yield was the result of a low conversion or competing reaction pathways. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
    Original languageEnglish
    Pages (from-to)1170-1179
    Number of pages9
    JournalChemBioChem: a European journal of chemical biology
    Volume8
    Issue number10
    DOIs
    Publication statusPublished - 9 Jul 2007

    Keywords

    • Nucleosides
    • Photoanomerisation
    • Photochemistry
    • Prebiotic
    • RNA

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