Excited-state hydrogen atom abstraction initiates the photochemistry of beta-2 '-deoxycytidine

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68081707%3A_____%2F15%3A00442385" target="_blank" >RIV/68081707:_____/15:00442385 - isvavai.cz</a>

Alternative codes found

RIV/00216224:14740/15:00082901

Result on the web

<a href="http://dx.doi.org/10.1039/c4sc03761h" target="_blank" >http://dx.doi.org/10.1039/c4sc03761h</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c4sc03761h" target="_blank" >10.1039/c4sc03761h</a>

Result language

angličtina

Original language name

Excited-state hydrogen atom abstraction initiates the photochemistry of beta-2 '-deoxycytidine

Original language description

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 prolongedUV-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 pyrimidi

Czech name

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Czech description

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Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

BO - Biophysics

OECD FORD branch

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Project

Result was created during the realization of more than one project. More information in the Projects tab.

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2015

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Chemical Science

ISSN

2041-6520

e-ISSN

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Volume of the periodical

6

Issue of the periodical within the volume

3

Country of publishing house

GB - UNITED KINGDOM

Number of pages

9

Pages from-to

2035-2043

UT code for WoS article

000349832600056

EID of the result in the Scopus database

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