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@article{2240875,
author = {GonzalezandOlvera, Julio C and Fiala, Radovan and Pless, Reynaldo C},
article_number = {30},
doi = {http://dx.doi.org/10.1002/slct.202200835},
keywords = {nucleobases; protonation; duplex DNA; oligonucleotides; basicity},
language = {eng},
issn = {2365-6549},
journal = {ChemistrySelect},
title = {Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine Base Pairs in Duplex Oligodeoxyribonucleotides},
url = {https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202200835},
volume = {7},
year = {2022}
}
TY - JOUR
ID - 2240875
AU - Gonzalez-Olvera, Julio C - Fiala, Radovan - Pless, Reynaldo C
PY - 2022
TI - Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine Base Pairs in Duplex Oligodeoxyribonucleotides
JF - ChemistrySelect
VL - 7
IS - 30
SP - 202200835
EP - 202200835
PB - Wiley Online Library
SN - 23656549
KW - nucleobases
KW - protonation
KW - duplex DNA
KW - oligonucleotides
KW - basicity
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/slct.202200835
N2 - NMR- and UV-monitored acid titrations conducted on short model oligodeoxyribonucleotide duplexes demonstrate the protonation of guanine:5-methylcytosine and guanine:cytosine base pairs at the O-2 position of the cytosine base, at pH values close to 7, without disruption of the general duplex structure. In the NMR technique, this protonation transition is most clearly observed by monitoring the 5-methylcytosine-H6 resonance, while pH effects on the 5-methylcytosine methyl group, on guanine-H8, and on the cytosine-H5 and -H6 resonances are small. The local sequences G(Me)CG, (TCT)-C-Me, and TCT show decreasing basicity, in this order. The basicity of the G:C-Me base pair is almost unaffected by ionic strength. Under more acidic conditions, adenine:thymine base pairs may be similarly protonated at the adenine base. Hydrogens on thymine bases contained in single-stranded oligonucleotides are strongly affected by the protonation of near-by bases. The results posit that canonical double-stranded DNA is protonated to a significant extent at certain sites under physiological conditions.
ER -
GONZALEZ-OLVERA, Julio C, Radovan FIALA a Reynaldo C PLESS. Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine Base Pairs in Duplex Oligodeoxyribonucleotides. \textit{ChemistrySelect}. Wiley Online Library, 2022, roč.~7, č.~30, s.~202200835-202200846. ISSN~2365-6549. Dostupné z: https://dx.doi.org/10.1002/slct.202200835.
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