Nonenzymatic oligomerization on templates containing phosphodiester-linked acyclic glycerol nucleic acid analogues

John C. Chaput, Christopher Switzer

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)464-470
Number of pages7
JournalJournal of Molecular Evolution
Volume51
Issue number5
DOIs
StatePublished - Jan 1 2000

Keywords

  • Chemical evolution
  • Pre-RNA
  • Template-directed oligomerization

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Molecular Biology
  • Genetics

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