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Chemial evolution

XVIII. Synthesis of Pyrimidines from Guanidine and Cyanoacetaldehyde

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Summary

Cyanoacetaldehyde condenses with guanidine in dilute aqueous solution to form 2,4-diaminopyrimidine which in turn is hydrolyzed to cytosine and uracil. The concentration of reagents required for the synthesis of 2,4-diaminopyrimidine is quite low, and cyanoacetadehyde is expected to have been present on the primitive earth since it is formed by the hydrolysis of cyanoacetylene. The stability of cyanoacetaldehyde and its aldol dimer to hydrolysis is 103 times that of cyanoacetylene. The half life for guanidine hydrolysis is 105–108 years at pH 9. The prebiotic synthesis of pyrimidines from cyanoacetaldehyde and guanidine is preferred over the previously proposed route from cyanoacetylene and cyanate because of the greater stability of the reactants.

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Authors and Affiliations

  1. Department of Chemistry, Rensselaer Polytechnic Institute, 12181, Troy, New York, USA

    J. P. Ferris, O. S. Zamek, A. M. Altbuch & H. Freiman

Authors
  1. J. P. Ferris
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  2. O. S. Zamek
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  3. A. M. Altbuch
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  4. H. Freiman
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Additional information

For the previous paper in this series see Ferriset al. (1974).

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Ferris, J.P., Zamek, O.S., Altbuch, A.M. et al. Chemial evolution. J Mol Evol 3, 301–309 (1974). https://doi.org/10.1007/BF01796045

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  • DOI: https://doi.org/10.1007/BF01796045

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