Synthesis of 2'-deoxycytidine and its triphosphate bearing tryptophan-based imidazolinone fluorophore for environment sensitive fluorescent labelling of DNA

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F18%3A10384669" target="_blank" >RIV/00216208:11310/18:10384669 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/18:00498550
Result on the web
<a href="https://doi.org/10.1016/j.tet.2018.09.061" target="_blank" >https://doi.org/10.1016/j.tet.2018.09.061</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tet.2018.09.061" target="_blank" >10.1016/j.tet.2018.09.061</a>

Result language
angličtina
Original language name
Synthesis of 2'-deoxycytidine and its triphosphate bearing tryptophan-based imidazolinone fluorophore for environment sensitive fluorescent labelling of DNA
Original language description
We synthesized 2'-deoxycytidine and the corresponding nucleoside triphosphate bearing (indol-3-yl) methylene-2-methyl-5-oxo-4,5-dihydroimidazol-1-yl group (a tryptophan-based fluorophore from cyan fluorescent protein) linked through a propargyl group at position 5. The fluorophore is weakly solvatochromic, sensitive to pH, and, as a molecular rotor, it is highly sensitive to viscosity. In low viscosity solvents, the fluorescence is very weak, whereas in more viscous environment it lights up. Primer extension or PCR using the modified dC(Trp)TP and KOD XL DNA polymerase was used for construction of labelled oligonucleotides and DNA. Preliminary study showed a 2-fold increase of fluorescence of labelled ON probe in presence of single strand-binding protein indicating a potential of this label for sensing of protein-DNA interactions.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry

Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2018
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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