title: Generation of RNA molecules by a base-catalysed click-like reaction.
abstract: The problem of the abiotic origin of RNA from prebiotically plausible compounds remains unsolved. As a potential partial solution, we report the spontaneous polymerization of 3',5'-cyclic GMP in water, in formamide, in dimethylformamide, and (in water) in the presence of a Brønsted base such as 1,8-diazabicycloundec-7-ene. The reaction is untemplated, does not require enzymatic activities, is thermodynamically favoured and selectively yields 3',5'-bonded ribopolymers containing as many as 25 nucleotides. We propose a reaction pathway on the basis of 1) the measured stacking of the 3',5'-cyclic monomers, 2) the activation by Brønsted bases, 3) the determination (by MALDI-TOF mass spectrometry, by (31)P NMR, and by specific ribonucleases) of the molecular species produced. The reaction pathway has several of the attributes of a click-like reaction.
authors.affiliation: Istituto di Biologia e Patologia Molecolari, CNR, Piazzale Aldo Moro 5, 00185 Rome, Italy.
authors.forename: Giovanna
authors.initials: G
authors.lastname: Costanzo
authors.forename: Raffaele
authors.initials: R
authors.lastname: Saladino
authors.forename: Giorgia
authors.initials: G
authors.lastname: Botta
authors.forename: Alessandra
authors.initials: A
authors.lastname: Giorgi
authors.forename: Anita
authors.initials: A
authors.lastname: Scipioni
authors.forename: Samanta
authors.initials: S
authors.lastname: Pino
authors.forename: Ernesto
authors.initials: E
authors.lastname: Di Mauro
mesh_terms: D002384:Catalysis; D057930:Click Chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D058105:Polymerization; D012313:RNA / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D012313:RNA