Origin of informational polymers. Differential stability of 3'- and 5'-phosphoester bonds in deoxy monomers and oligomers

J Biol Chem. 2005 Oct 21;280(42):35658-69. doi: 10.1074/jbc.M504537200. Epub 2005 Jul 21.

Abstract

To survive, an informational macromolecule must solve the major problem set by its very polymeric nature: instability. This is especially true in prebiotic terms because of the presumed initial absence of protective structures (proteins, lipids, etc.). We have analyzed the stability of the beta-glycosidic and of the 3'- and 5'-phosphoester bonds in both deoxy monomers and deoxy oligomers under a large set of conditions. The results show a strong dependence of the relative stability of these bonds on the physico-chemical environment. A set of conditions has been identified in which the stability of polymers becomes comparable with that of the precursor monomers. In certain instances the stability of the 5'-phosphoester bond is even higher in the polymer than in the mononucleotide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Base Sequence
  • Biotechnology / methods*
  • Catalysis
  • Chromatography, High Pressure Liquid
  • DNA / chemistry
  • Deoxyadenosines / chemistry
  • Esters / chemistry*
  • Formamides / chemistry
  • Glycosides / chemistry
  • Kinetics
  • Lipids / chemistry
  • Macromolecular Substances / chemistry
  • Models, Chemical
  • Molecular Sequence Data
  • Molecular Structure
  • Nucleotides / chemistry
  • Oligonucleotides / chemistry
  • Polymers / chemistry*
  • RNA / chemistry
  • Temperature
  • Time Factors

Substances

  • Deoxyadenosines
  • Esters
  • Formamides
  • Glycosides
  • Lipids
  • Macromolecular Substances
  • Nucleotides
  • Oligonucleotides
  • Polymers
  • formamide
  • RNA
  • DNA