Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling

0382138 - ÚOCHB 2013 RIV DE eng J - Journal Article
Raindlová, Veronika - Pohl, Radek - Klepetářová, Blanka - Havran, Luděk - Šimková, Eva - Horáková Brázdilová, Petra - Pivoňková, Hana - Fojta, Miroslav - Hocek, Michal
Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling.
ChemPlusChem. Roč. 77, č. 8 (2012), s. 652-662. ISSN 2192-6506. E-ISSN 2192-6506
R&D Projects: GA AV ČR(CZ) IAA400040901; GA ČR GBP206/12/G151
Institutional research plan: CEZ:AV0Z40550506; CEZ:AV0Z50040702
Keywords : DNA * oligonucleotides * polymerase * hydrazones * nucleotides
Subject RIV: CC - Organic Chemistry

5-(5-Formylthiophen-2-yl)cytosine and -7-deazaadenosine 2'-deoxyribonucleosides and their triphosphates were converted to the 2,4-dinitrophenyl- or nitrobenzofurazanyl hydrazones. The hydrazone-modified dNTPs were enzymatically incorporated to DNA by polymerase catalyzed primer extension. This direct incorporation of hydrazone-linked dNTPs was compared to previously reported incorporation of aldehyde-modified dNTPs followed by post-synthetic hydrazone-formation on DNA. Electrochemical study the nitroarylhydrazone-linked nucleosides and DNA was performed confirming the potential of the hydrazones, nitroaryls and benzofurazane groups for redox labelling of DNA.
Permanent Link: http://hdl.handle.net/11104/0212447