One-Pot TiO₂-Catalyzed Synthesis of Nucleic Bases and Acyclonucleosides from Formamide: Implications for the Origin of Life

A novel one-pot TiO₂-catalyzed synthesis of nucleobases and acyclonucleosides from formamide is reported. Since formamide can be formed under prebiotic conditions, these reactions have implications for the origin of life. While a number of purine derivatives have been found as products of non-TiO₂-c...

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Bibliographic Details
Published in:Chembiochem : a European journal of chemical biology 2003-06, Vol.4 (6), p.514-521
Main Authors: Saladino, Raffaele, Ciambecchini, Umberto, Crestini, Claudia, Costanzo, Giovanna, Negri, Rodolfo, Di Mauro, Ernesto
Format: Article
Language:English
Subjects:
Base Sequence
Catalysis
formamide
Formamides - chemistry
Mass Spectrometry
Molecular Structure
nucleic acids
nucleobases
Nucleosides - chemical synthesis
Nucleosides - chemistry
Oligonucleotides - chemistry
Oligonucleotides - genetics
Origin of Life
prebiotic syntheses
Purines - chemical synthesis
Purines - chemistry
Pyrimidines - chemical synthesis
Pyrimidines - chemistry
Titanium - chemistry
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Summary:A novel one-pot TiO₂-catalyzed synthesis of nucleobases and acyclonucleosides from formamide is reported. Since formamide can be formed under prebiotic conditions, these reactions have implications for the origin of life. While a number of purine derivatives have been found as products of non-TiO₂-catalyzed reactions, important compounds that would not otherwise occur (namely, thymine, 5hydroxymethyluracil, and acyclonucleosides) are formed in acceptable yields by TiO₂-catalyzed reactions. Moreover, TiO₂ selectively affects the rates of degradation of nucleobases, as single units and when embedded in polynucleotides.
ISSN:1439-4227
1439-7633
DOI:10.1002/cbic.200300567