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Synthesis of functionalized nucleosides and nucleotides and their incorporation into DNA
Balintová, Jana ; Hocek, Michal (advisor) ; Stiborová, Marie (referee) ; Bartošík, Martin (referee)
This PhD thesis describes the synthesis of modified DNA containing electrochemical active labels such as anthraquinone, benzofurazane, azide and nitrophenyltriazole with the application in bioanalysis. The methodology of the construction of base-modified triphosphates based on Suzuki-Miyaura coupling of halogenated deoxynucleoside triphosphates with arylboronic acids, Sonogashira coupling of dNTPs with terminal acetylenes or triphosphorylation of modified nucleosides was developed. Enzymatic incorporation of functionalized dNTPs into DNA by primer extension experiment and the electrochemical properties of DNA bearing redox labels were studied by cyclic and square- wave voltammetry. At first anthraquinone was tested as an electrochemical label. Modified 2'-deoxynucleoside triphosphates bearing anthraquinone attached through an acetylene or propargylcarbamoyl linker at 5-position of 2'-deoxycytidine 5'-triphosphate and at the 7-position of 7-deaza-2'-deoxyadenosine-5'-triphosphate were prepared by Sonogashira cross-coupling. Enzymatic incorporation of the anthraquinone-labeled dNTPs into DNA by primer extension has been developed. The electrochemical properties of the anthraquinone- labeled nucleosides, dNTPs and DNA were studied by cyclic voltammetry which shows a reversible couple of peaks around...

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