Ribose Alters the Photochemical Properties of the Nucleobase in Thionated Nucleosides

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F68081707%3A_____%2F21%3A00544618" target="_blank" >RIV/68081707:_____/21:00544618 - isvavai.cz</a>
Alternative codes found
RIV/61989592:15640/21:73611192
Result on the web
<a href="https://pubs.acs.org/doi/abs/10.1021/acs.jpclett.1c01384" target="_blank" >https://pubs.acs.org/doi/abs/10.1021/acs.jpclett.1c01384</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.jpclett.1c01384" target="_blank" >10.1021/acs.jpclett.1c01384</a>

Result language
angličtina
Original language name
Ribose Alters the Photochemical Properties of the Nucleobase in Thionated Nucleosides
Original language description
Substitution of exocyclic oxygen with sulfur was shown to substantially influence the properties of RNA/DNA bases, which are crucial for prebiotic chemistry and photodynamic therapies. Upon UV irradiation, thionucleobases were shown to efficiently populate triplet excited states and can be involved in characteristic photochemistry or generation of singlet oxygen. Here, we show that the photochemistry of a thionucleobase can be considerably modified in a nucleoside, that is, by the presence of ribose. Our transient absorption spectroscopy experiments demonstrate that thiocytosine exhibits 5 times longer excited-state lifetime and different excited-state absorption features than thiocytidine. On the basis of accurate quantum chemical simulations, we assign these differences to the dominant population of a shorter-lived triplet n pi* state in the nucleoside and longer-lived triplet pi pi* states in the nucleobase. This explains the distinctive photoanomerziation of thiocytidine and indicates that the nucleoside will be a less efficient phototherapeutic agent with regard to singlet oxygen generation.
Czech name
—
Czech description
—

Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10403 - Physical chemistry

Project
<a href="/en/project/GA21-23718S" target="_blank" >GA21-23718S: The fascinating physical chemistry of DNA studied by advanced computations</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Similar results(10)