The synthesis and stability of oligodeoxyribonucleotides containing the deoxyadenosine mimic 1-(2'-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide

W. Travis Johnson, Peiming Zhang, Donald E. Bergstrom

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Oligodeoxyribonucleotides containing the nucleoside analog 1-(2'-deoxy-β-D-ribofuranosyl) imidazole-4-carboxamide (1) were synthesized by solid phase phosphoramidite technology. Nucleoside 1, which contains a reactive exocyclic amide moiety, was incorporated into synthetic oligodeoxyribonucleotides with the use of a benzoyl protecting group. The corresponding oligodeoxyribonucleotides with dI or dA in the same position in the sequence were synthesized for UV comparison of helix-coil transitions. The thermal melting studies indicate that 1, which could conceptually adopt either a dA- or a dI-like hydrogen bond configuration, pairs with significantly higher affinity to T than to dC. Nucleoside 1 further resembles dA in the relative order of its base pairing preferences (T > dG > dA > dC), but may be less discriminating than dA in its bias for base pairing with T over dG.

Original languageEnglish (US)
Pages (from-to)559-567
Number of pages9
JournalNucleic Acids Research
Volume25
Issue number3
DOIs
StatePublished - 1997
Externally publishedYes

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Oligodeoxyribonucleotides
Nucleosides
Base Pairing
Pair Bond
Amides
Freezing
Hydrogen
Hot Temperature
Technology
imidazole-4-carboxamide
neurotensin mimic 1
neurotensin mimic 2
2'-deoxyadenosine

ASJC Scopus subject areas

  • Genetics

Cite this

The synthesis and stability of oligodeoxyribonucleotides containing the deoxyadenosine mimic 1-(2'-deoxy-β-D-ribofuranosyl)imidazole-4-carboxamide. / Johnson, W. Travis; Zhang, Peiming; Bergstrom, Donald E.

In: Nucleic Acids Research, Vol. 25, No. 3, 1997, p. 559-567.

Research output: Contribution to journalArticle

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