Formamide chemistry provides a unitary system by gathering all of the precursors needed to synthesise pregenetic informational polymers in a single milieu. This is not observed with HCN chemistry. With common catalysts, formamide affords all of the precursor nucleobases, photochemically condenses into acyclonucleosides, favours transphosphorylation and enhances micellar aggregation of surfactants. Also, formamide provides a set of physicochemical conditions that thermodynamically favour the polymeric state of nucleotides over the monomers. In the origin-of-informational-polymers scenario, formamide acts in every step, the least characterised being the set of its reactions with phosphates. On this matter, we report two complementary sets of results: 1) the synthesis of prebiotic precursors from formamide, which are catalysed by soluble and mineral phosphates - we observed the formation of rich mixtures that include uracil, 9H-purine, cytosine, dihydrouracil, hypoxanthine, adenosine, urea, parabanic acid, the amino acid H-formylglycine and the peptide-condensing agent carbodiimide; and 2) the protection of ribo-and deoxyribophosphoester bonds by phosphates. The relevance of these effects with respect to the origin of informational polymers is discussed. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.

Origin of informational polymers: The concurrent roles of formamide and phosphates

CRESTINI, Claudia
2006

Abstract

Formamide chemistry provides a unitary system by gathering all of the precursors needed to synthesise pregenetic informational polymers in a single milieu. This is not observed with HCN chemistry. With common catalysts, formamide affords all of the precursor nucleobases, photochemically condenses into acyclonucleosides, favours transphosphorylation and enhances micellar aggregation of surfactants. Also, formamide provides a set of physicochemical conditions that thermodynamically favour the polymeric state of nucleotides over the monomers. In the origin-of-informational-polymers scenario, formamide acts in every step, the least characterised being the set of its reactions with phosphates. On this matter, we report two complementary sets of results: 1) the synthesis of prebiotic precursors from formamide, which are catalysed by soluble and mineral phosphates - we observed the formation of rich mixtures that include uracil, 9H-purine, cytosine, dihydrouracil, hypoxanthine, adenosine, urea, parabanic acid, the amino acid H-formylglycine and the peptide-condensing agent carbodiimide; and 2) the protection of ribo-and deoxyribophosphoester bonds by phosphates. The relevance of these effects with respect to the origin of informational polymers is discussed. © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10278/3710880
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