title: A high-yielding, strictly regioselective prebiotic purine nucleoside formation pathway.
abstract: The origin of life is believed to have started with prebiotic molecules reacting along unidentified pathways to produce key molecules such as nucleosides. To date, a single prebiotic pathway to purine nucleosides had been proposed. It is considered to be inefficient due to missing regioselectivity and low yields. We report that the condensation of formamidopyrimidines (FaPys) with sugars provides the natural N-9 nucleosides with extreme regioselectivity and in good yields (60%). The FaPys are available from formic acid and aminopyrimidines, which are in turn available from prebiotic molecules that were also detected during the Rosetta comet mission. This nucleoside formation pathway can be fused to sugar-forming reactions to produce pentosides, providing a plausible scenario of how purine nucleosides may have formed under prebiotic conditions.
authors.affiliation: Ludwig-Maximilians-Universität München, Department für Chemie, D-81377 Munich, Germany.
authors.forename: Sidney
authors.initials: S
authors.lastname: Becker
authors.affiliation: Ludwig-Maximilians-Universität München, Department für Chemie, D-81377 Munich, Germany.
authors.forename: Ines
authors.initials: I
authors.lastname: Thoma
authors.affiliation: Ludwig-Maximilians-Universität München, Department für Chemie, D-81377 Munich, Germany.
authors.forename: Amrei
authors.initials: A
authors.lastname: Deutsch
authors.affiliation: Ludwig-Maximilians-Universität München, Department für Chemie, D-81377 Munich, Germany.
authors.forename: Tim
authors.initials: T
authors.lastname: Gehrke
authors.affiliation: Ludwig-Maximilians-Universität München, Department für Chemie, D-81377 Munich, Germany.
authors.forename: Peter
authors.initials: P
authors.lastname: Mayer
authors.affiliation: Ludwig-Maximilians-Universität München, Department für Chemie, D-81377 Munich, Germany.
authors.forename: Hendrik
authors.initials: H
authors.lastname: Zipse
authors.affiliation: Ludwig-Maximilians-Universität München, Department für Chemie, D-81377 Munich, Germany. thomas.carell@cup.uni-muenchen.de.
authors.forename: Thomas
authors.initials: T
authors.lastname: Carell
mesh_terms: D005561:Formates / Q000737:chemistry; D019110:Meteoroids; D000069497:Origin of Life; D056692:Prebiotics; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011743:Pyrimidines / Q000737:chemistry; D012313:RNA / Q000737:chemistry*
chemical_list: D005561:Formates; D056692:Prebiotics; D011684:Purine Nucleosides; D011743:Pyrimidines; C030544:formic acid; D012313:RNA