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@article{1314691,
author = {Yurenko, Yevgen and Novotný, Jan and Sklenář, Vladimír and Marek, Radek},
article_location = {WEINHEIM},
article_number = {49},
doi = {http://dx.doi.org/10.1002/chem.201502977},
keywords = {density functional calculations; DNA; fluorinated compounds; G-quadruplexes; relaxed force constants},
language = {eng},
issn = {0947-6539},
journal = {Chemistry - A European Journal},
title = {Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions},
url = {http://dx.doi.org/10.1002/chem.201502977},
volume = {21},
year = {2015}
}
TY - JOUR
ID - 1314691
AU - Yurenko, Yevgen - Novotný, Jan - Sklenář, Vladimír - Marek, Radek
PY - 2015
TI - Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions
JF - Chemistry - A European Journal
VL - 21
IS - 49
SP - 17933-17943
EP - 17933-17943
PB - Wiley
SN - 09476539
KW - density functional calculations
KW - DNA
KW - fluorinated compounds
KW - G-quadruplexes
KW - relaxed force constants
UR - http://dx.doi.org/10.1002/chem.201502977
L2 - http://dx.doi.org/10.1002/chem.201502977
N2 - Intrinsic structural features and energetics of nucleotides containing variously fluorinated sugars as potential building blocks of DNA duplexes and quadruplexes are explored systematically using the modern methods of density functional theory (DFT) and quantum chemical topology (QCT). Our results suggest that fluorination at the 2'-B or 2'-A,B positions somewhat stabilizes in vacuo the AI relative to the BI conformations. In contrast, substitution of the CF2 group for the O4' atom (O4'-CF2 modification) leads to a preference of the BI relative to AI DNA-like conformers. All the studied modifications result in a noticeable increase in the stability of the glycosidic bond [estimated by the relaxed force constants (RFC) approach], with particularly encouraging results for the O4'-CF2 derivative. Consequently, the O4'-CF2 modified systems are suggested and explored as promising scaffolds for the development of duplex and quadruplex structures with reduced propensity to form abasic lesions and to undergo DNA damage.
ER -
YURENKO, Yevgen, Jan NOVOTNÝ, Vladimír SKLENÁŘ a Radek MAREK. Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions. \textit{Chemistry - A European Journal}. WEINHEIM: Wiley, roč.~21, č.~49, s.~17933-17943. ISSN~0947-6539. doi:10.1002/chem.201502977. 2015.
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