Journal
BIOCHEMISTRY
Volume 39, Issue 19, Pages 5886-5892Publisher
AMER CHEMICAL SOC
DOI: 10.1021/bi992630n
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To investigate cytosine protonation and its influence on the sequence-dependent thermal stability of DNA triplexes in detail, we have employed homo- and heteronuclear NMR experiments on specifically N-15-labeled oligodeoxynucleotides that were designed to fold into intramolecular triple helices of the pyrimidine motif under appropriate conditions. These experiments reveal that cytosines in central positions of the tripler are significantly protonated even at neutral pH. However, semiprotonation points for individual cytosine bases as determined from pH-dependent measurements show considerable differences depending on their position. Thus, protonation is disfavored for adjacent cytosines or for cytosines at the tripler termini, resulting in a smaller contribution to the overall free energy of the triple helical system. In contrast, protonation of the base upon substitution of 5-methylcytosine for cytosine in the tripler third strand is only affected to a minor extent, and tripler stabilization by the methyl substituent is shown to primarily arise from stacking energies and/or hydrophobic effects.
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