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A high-yielding, strictly regioselective prebiotic purine nucleoside formation pathway

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Science  13 May 2016:
Vol. 352, Issue 6287, pp. 833-836
DOI: 10.1126/science.aad2808

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  • RE: About the prebiotic routes to nucleosides
    • Raffaele Saladino, Chair of Organic Chemistry, University of Tuscia, Viterbo, Italy
    • Other Contributors:
      • Ernesto Di Mauro, Chair of Molecular Biology, University of Rome, La Sapienza, Italy

    The difficulty of the abiotic synthesis of nucleosides essentially resides in the formation of the glycosidic bond between nucleobases and sugars. We have read with interest the paper describing the "prebiotic" purine nucleoside formation pathway, recently appeared in Science (1). The authors state that at present the "only prebiotic route to purine nucleosides proposes the condensation of the complete nucleobase, such as adenine, with ribose in the molten state", which entails regiochemistry problems in the glycosilation of the purine heterocycle.
    An elegant and complex series of reactions was consequently developed, describing the condensation of formamidopyrimidines with sugars. Formamidopyrimidine were actually previously shown to be produced by formamide degradation of purine nucleosides (2). Is this the only or the simplest way to obtain purine nucleosides with regio-selectivity, as stated by the authors? Data actually exist for solid alternatives.
    Acyclonucleosides with the correct N9 regioselectivity were produced from formyl purines by a formose condensation-like process (3). In addition, the one-pot total synthesis of purine and pyrimidine nucleobases (uridine, cytidine, thymidine, adenosine) with the right regiochemistry was obtained, directly from formamide (4). Two alternative scenarios are thus known and available: the reaction between preformed nucleobases and sugars (1, 5), and the one-pot synthesis of nucleosides directly f...

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    Competing Interests: None declared.