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Journal of Molecular Evolution

, Volume 51, Issue 5, pp 464–470 | Cite as

Nonenzymatic Oligomerization on Templates Containing Phosphodiester-Linked Acyclic Glycerol Nucleic Acid Analogues

  • John C.  Chaput
  • Christopher  Switzer

Abstract.

Nonenzymatic oligomerization reactions represent a model for studying the prebiotic replication of informational macromolecules. To explore the fitness of acyclic oligonucleotides in these reactions, we have synthesized a series of DNA hairpins appended with templates incorporating atactic glyceryl cytosine residues. Atactic glyceryl cytosine units are found to impede, but not to block, template-directed oligomerization of guanosine 5′-phosphoro-2-methylimidazole (2-MeImpG). Evidence suggests that both D and L glyceryl nucleoside configurations at a given template position contribute to product formation. The stability of DNA duplexes bearing isolated glyceryl cytosine residues has also been investigated. Duplex thermal denaturation experiments indicate that an atactic glyC · dG base-pair is intermediate in stability between a dC · dG pair and a dT · dG mismatch.

Key words: Template-directed oligomerization — Chemical evolution — Pre-RNA 

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Copyright information

© Springer-Verlag New York Inc. 2000

Authors and Affiliations

  • John C.  Chaput
    • 1
  • Christopher  Switzer
    • 1
  1. 1.Department of Chemistry, University of California, Riverside, CA 92521, USAUS

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