Equilibrium between a wobble and ionized base pair formed between fluorouracil and guanine in DNA as studied by proton and fluorine NMR

A synthetic oligonucleotide duplex containing the chemotherapeutic and mutagenic agent 5-fluorouracil paired with guanine has been studied in solution by proton and fluorine NMR. The 7-mer duplex containing a central FU.G base pair adopts a normal right-handed configuration. At low pH, the predomina...

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Published in:The Journal of biological chemistry 1988-10, Vol.263 (29), p.14794-14801
Main Authors: Sowers, L C, Eritja, R, Kaplan, B, Goodman, M F, Fazakerly, G V
Format: Article
Language:English
Subjects:
Base Composition
Biological and medical sciences
DNA
Fluorine
Fluorouracil
Fundamental and applied biological sciences. Psychology
Guanine
Hydrogen-Ion Concentration
Interactions. Associations
Intermolecular phenomena
Kinetics
Magnetic Resonance Spectroscopy - methods
Molecular biophysics
Molecular Structure
Nucleic Acid Conformation
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cited_by cdi_FETCH-LOGICAL-c496t-4255d1f064669bc33a2c40c64fe4ab7586de23321a6c442882f221e66e8301e13
cites cdi_FETCH-LOGICAL-c496t-4255d1f064669bc33a2c40c64fe4ab7586de23321a6c442882f221e66e8301e13
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container_issue 29
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container_title The Journal of biological chemistry
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creator Sowers, L C
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description A synthetic oligonucleotide duplex containing the chemotherapeutic and mutagenic agent 5-fluorouracil paired with guanine has been studied in solution by proton and fluorine NMR. The 7-mer duplex containing a central FU.G base pair adopts a normal right-handed configuration. At low pH, the predominant base-paired structure is wobble, whereas at higher pH an ionized structure in Watson-Crick geometry is observed. The two structures are in a pH-dependent equilibrium with one another with an apparent pK of 8.3 at 23 degrees C. This is the first demonstration of an equilibrium between two distinct base pairing schemes and the first demonstration of a negatively charged base pair in DNA.
doi_str_mv 10.1016/S0021-9258(18)68108-6
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ispartof The Journal of biological chemistry, 1988-10, Vol.263 (29), p.14794-14801
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source ScienceDirect (Online service)
subjects Base Composition
Biological and medical sciences
DNA
Fluorine
Fluorouracil
Fundamental and applied biological sciences. Psychology
Guanine
Hydrogen-Ion Concentration
Interactions. Associations
Intermolecular phenomena
Kinetics
Magnetic Resonance Spectroscopy - methods
Molecular biophysics
Molecular Structure
Nucleic Acid Conformation
title Equilibrium between a wobble and ionized base pair formed between fluorouracil and guanine in DNA as studied by proton and fluorine NMR
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