| SZABLA, Rafal Kazimierz, Jesus CAMPOS, Judit ŠPONEROVÁ, Jiří ŠPONER, Robert W. GORA a John D. SUTHERLAND. Excited-state hydrogen atom abstraction initiates the photochemistry of beta-2 '-deoxycytidine. CHEMICAL SCIENCE. Cambridge: ROYAL SOC CHEMISTRY, 2015, roč. 6, č. 3, s. 2035-2043. ISSN 2041-6520. Dostupné z: https://dx.doi.org/10.1039/c4sc03761h. |
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@article{1299597,
author = {Szabla, Rafal Kazimierz and Campos, Jesus and Šponerová, Judit and Šponer, Jiří and Gora, Robert W. and Sutherland, John D.},
article_location = {Cambridge},
article_number = {3},
doi = {http://dx.doi.org/10.1039/c4sc03761h},
keywords = {ULTRAFAST IR SPECTROSCOPY; CONICAL INTERSECTIONS; CYTOSINE DERIVATIVES; PREBIOTIC SYNTHESIS; BUILDING-BLOCKS; NUCLEIC-ACIDS; GAS-PHASE; DYNAMICS; NUCLEOSIDES; DNA},
language = {eng},
issn = {2041-6520},
journal = {CHEMICAL SCIENCE},
title = {Excited-state hydrogen atom abstraction initiates the photochemistry of beta-2 '-deoxycytidine},
url = {http://pubs.rsc.org/en/content/articlepdf/2015/SC/C4SC03761H},
volume = {6},
year = {2015}
}
TY - JOUR
ID - 1299597
AU - Szabla, Rafal Kazimierz - Campos, Jesus - Šponerová, Judit - Šponer, Jiří - Gora, Robert W. - Sutherland, John D.
PY - 2015
TI - Excited-state hydrogen atom abstraction initiates the photochemistry of beta-2 '-deoxycytidine
JF - CHEMICAL SCIENCE
VL - 6
IS - 3
SP - 2035-2043
EP - 2035-2043
PB - ROYAL SOC CHEMISTRY
SN - 20416520
KW - ULTRAFAST IR SPECTROSCOPY
KW - CONICAL INTERSECTIONS
KW - CYTOSINE DERIVATIVES
KW - PREBIOTIC SYNTHESIS
KW - BUILDING-BLOCKS
KW - NUCLEIC-ACIDS
KW - GAS-PHASE
KW - DYNAMICS
KW - NUCLEOSIDES
KW - DNA
UR - http://pubs.rsc.org/en/content/articlepdf/2015/SC/C4SC03761H
L2 - http://pubs.rsc.org/en/content/articlepdf/2015/SC/C4SC03761H
N2 - Understanding the effects of ultraviolet radiation on nucleotides in solution is an important step towards a comprehensive description of the photochemistry of nucleic acids and their constituents. Apart from having implications for mutagenesis and DNA photoprotection mechanisms, the photochemistry of cytidines is a central element in UV-assisted syntheses of pyrimidine nucleotides under prebiotically plausible conditions. In this contribution, we present UV-irradiation experiments of beta-2'-deoxycytidine in aqueous solution involving H-D exchange followed by NMR spectroscopic analysis of the photoproducts. We further elucidate the outcome of these experiments by means of high-level quantum chemical calculations. In particular, we show that prolonged UV-irradiation of cytidine may lead to H-C1' hydrogen atom abstraction by the carbonyl oxygen atom of cytosine. This process may enable photoanomerisation and nucleobase loss, two previously unexplained photoreactions observed in pyrimidine nucleotides.
ER -
SZABLA, Rafal Kazimierz, Jesus CAMPOS, Judit ŠPONEROVÁ, Jiří ŠPONER, Robert W. GORA a John D. SUTHERLAND. Excited-state hydrogen atom abstraction initiates the photochemistry of beta-2 '-deoxycytidine. \textit{CHEMICAL SCIENCE}. Cambridge: ROYAL SOC CHEMISTRY, 2015, roč.~6, č.~3, s.~2035-2043. ISSN~2041-6520. Dostupné z: https://dx.doi.org/10.1039/c4sc03761h.
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