Structural and dynamic properties of a fluorouracil-adenine base pair in DNA studied by proton NMR.

Lawrence Sowers, R. Eritja, B. E. Kaplan, M. F. Goodman, G. V. Fazakerley

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

An oligodeoxynucleotide duplex containing the chemotherapeutic agent 5-fluorouracil (FU) has been constructed by solid phase phosphotriester synthesis and has been studied in solution by proton NMR. In this study, we provide the first structural characterization of a DNA complex containing a FU.A base pair. It has been determined that the 7-mer duplex containing a central FU.A base pair adopts a normal right-handed configuration and the A residue in the FU.A pair is oriented in the normal anticonfiguration giving a Watson-Crick base pair. The significant difference between T.A and FU.A base pairs is dynamic, not structural: the FU.A base pair opens faster than normal base pairs in the oligonucleotide studied. We provide evidence that the FU.A base pair has a significantly enhanced opening rate resulting form decreased stacking of the 5-fluorouracil residue and not from the enhanced acidity of the 5'-fluorouracil imino proton.

Original languageEnglish (US)
Pages (from-to)15436-15442
Number of pages7
JournalJournal of Biological Chemistry
Volume262
Issue number32
StatePublished - Nov 15 1987
Externally publishedYes

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Adenine
Base Pairing
Fluorouracil
Protons
Nuclear magnetic resonance
DNA
Solid-Phase Synthesis Techniques
Oligodeoxyribonucleotides
Structural dynamics
Acidity
Oligonucleotides

ASJC Scopus subject areas

  • Biochemistry

Cite this

Sowers, L., Eritja, R., Kaplan, B. E., Goodman, M. F., & Fazakerley, G. V. (1987). Structural and dynamic properties of a fluorouracil-adenine base pair in DNA studied by proton NMR. Journal of Biological Chemistry, 262(32), 15436-15442.

Structural and dynamic properties of a fluorouracil-adenine base pair in DNA studied by proton NMR. / Sowers, Lawrence; Eritja, R.; Kaplan, B. E.; Goodman, M. F.; Fazakerley, G. V.

In: Journal of Biological Chemistry, Vol. 262, No. 32, 15.11.1987, p. 15436-15442.

Research output: Contribution to journalArticle

Sowers, L, Eritja, R, Kaplan, BE, Goodman, MF & Fazakerley, GV 1987, 'Structural and dynamic properties of a fluorouracil-adenine base pair in DNA studied by proton NMR.', Journal of Biological Chemistry, vol. 262, no. 32, pp. 15436-15442.
Sowers, Lawrence ; Eritja, R. ; Kaplan, B. E. ; Goodman, M. F. ; Fazakerley, G. V. / Structural and dynamic properties of a fluorouracil-adenine base pair in DNA studied by proton NMR. In: Journal of Biological Chemistry. 1987 ; Vol. 262, No. 32. pp. 15436-15442.
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