Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine
Base Pairs in Duplex Oligodeoxyribonucleotides

J 2022

Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine Base Pairs in Duplex Oligodeoxyribonucleotides

GONZALEZ-OLVERA, Julio C, Radovan FIALA and Reynaldo C PLESS

Basic information

Original name

Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine Base Pairs in Duplex Oligodeoxyribonucleotides

Authors

GONZALEZ-OLVERA, Julio C, Radovan FIALA (203 Czech Republic, guarantor, belonging to the institution) and Reynaldo C PLESS

Edition

ChemistrySelect, Wiley Online Library, 2022, 2365-6549

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10406 Analytical chemistry

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 2.100

RIV identification code

RIV/00216224:14740/22:00127512

Organization unit

Central European Institute of Technology

DOI

http://dx.doi.org/10.1002/slct.202200835

UT WoS

000837720900001

Keywords in English

nucleobases; protonation; duplex DNA; oligonucleotides; basicity

Abstract

V originále

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.

Links

90127, large research infrastructures

Name: CIISB II

Citovat

GONZALEZ-OLVERA, Julio C, Radovan FIALA and Reynaldo C PLESS. Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine Base Pairs in Duplex Oligodeoxyribonucleotides. ChemistrySelect. Wiley Online Library, 2022, vol. 7, No 30, p. 202200835-202200846. ISSN 2365-6549. Available from: https://dx.doi.org/10.1002/slct.202200835.

@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 and Reynaldo C PLESS. Protonation of Guanine:5-Methylcytosine and Guanine:Cytosine Base Pairs in Duplex Oligodeoxyribonucleotides. \textit{ChemistrySelect}. Wiley Online Library, 2022, vol.~7, No~30, p.~202200835-202200846. ISSN~2365-6549. Available from: https://dx.doi.org/10.1002/slct.202200835.

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