title: On the prebiotic synthesis of ribonucleotides: photoanomerisation of cytosine nucleosides and nucleotides revisited.
abstract: Recent work has emphasised the importance of D-ribose aminooxazoline 1 in the synthesis of cytidine ribonucleosides under potentially prebiotic conditions. Upon treatment with cyanoacetylene, 1 is transformed into alpha-D-cytidine (alpha-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 beta-D-nucleosides required to make RNA would be realised. Photoanomerisation of alpha-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.
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
authors.forename: Matthew W
authors.initials: MW
authors.lastname: Powner
authors.forename: Carole
authors.initials: C
authors.lastname: Anastasi
authors.forename: Michael A
authors.initials: MA
authors.lastname: Crowe
authors.forename: Alastair L
authors.initials: AL
authors.lastname: Parkes
authors.forename: Jim
authors.initials: J
authors.lastname: Raftery
authors.forename: John D
authors.initials: JD
authors.lastname: Sutherland
mesh_terms: D001671:Biochemistry / Q000379:methods; D002219:Carbamates / Q000737:chemistry; D003562:Cytidine / Q000737:chemistry; D003596:Cytosine / Q000737:chemistry*; D008027:Light; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D008956:Models, Chemical; D009705:Nucleosides / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry; D012313:RNA / Q000737:chemistry; D012265:Ribonucleotides / Q000737:chemistry*; D013997:Time Factors
chemical_list: D002219:Carbamates; D009705:Nucleosides; D011714:Pyrans; D011741:Pyrimidine Nucleosides; D011743:Pyrimidines; D012265:Ribonucleotides; D003562:Cytidine; D012313:RNA; D003596:Cytosine