Substituting CF2 for O4' in Components of Nucleic Acids: Towards Systems with Reduced Propensity to Form Abasic Lesions

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Publikace nespadá pod Filozofickou fakultu, ale pod Středoevropský technologický institut. Oficiální stránka publikace je na webu muni.cz.
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YURENKO Yevgen NOVOTNÝ Jan SKLENÁŘ Vladimír MAREK Radek

Rok publikování 2015
Druh Článek v odborném periodiku
Časopis / Zdroj Chemistry - A European Journal
Fakulta / Pracoviště MU

Středoevropský technologický institut

Citace
www DOI: 10.1002/chem.201502977
Doi http://dx.doi.org/10.1002/chem.201502977
Obor Fyzikální chemie a teoretická chemie
Klíčová slova density functional calculations; DNA; fluorinated compounds; G-quadruplexes; relaxed force constants
Přiložené soubory
Popis 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.
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