title: Synthesis of cytidine ribonucleotides by stepwise assembly of the heterocycle on a sugar phosphate.
abstract: Although various syntheses of the nucleic acid bases exist and ribose is a product of the formose reaction, no prebiotically plausible methods for attaching pyrimidine bases to ribose to give nucleosides have been described. Kinetic and thermodynamic factors are thought to mitigate against such condensation reactions in aqueous solution. This inability to produce pyrimidine nucleosides and hence nucleotides is a major stumbling block of the "RNA World" hypothesis and has led to suggestions of alternative nucleic acids as evolutionary precursors to RNA. Here, we show that a process in which the base is assembled in stages on a sugar phosphate can produce cytidine nucleotides. The sequential action of cyanamide and cyanoacetylene on arabinose-3-phosphate produces cytidine-2',3'-cyclophosphate and arabinocytidine-3'-phosphate.
authors.affiliation: Department of Chemistry The University of Manchester Oxford Road, Manchester M13 9PL, UK.
authors.forename: Abdul-Aziz
authors.initials: AA
authors.lastname: Ingar
authors.forename: Richard W A
authors.initials: RW
authors.lastname: Luke
authors.forename: Barry R
authors.initials: BR
authors.lastname: Hayter
authors.forename: John D
authors.initials: JD
authors.lastname: Sutherland
mesh_terms: D003562:Cytidine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012265:Ribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D013403:Sugar Phosphates / Q000737:chemistry*
chemical_list: D012265:Ribonucleotides; D013403:Sugar Phosphates; D003562:Cytidine