Synthesis of nucleosides and nucleoside triphosphates bearing anthraquinone substituents as redox probes and their enzymatic incorporation to DNA

0361544 - ÚOCHB 2012 CZ eng C - Conference Paper (international conference)
Balintová, Jana - Havran, Luděk - Fojta, Miroslav - Hocek, Michal
Synthesis of nucleosides and nucleoside triphosphates bearing anthraquinone substituents as redox probes and their enzymatic incorporation to DNA.
Chemistry of Nucleic Acid Components. 15th Symposium. Praha: Institute of Organic Chemistry and Biochemistry AS CR, v. v. i., 2011 - (Hocek, M.), s. 297-299. Collection Symposium Series, 12. ISBN 978-80-86241-37-1.
[Chemistry of Nucleic Acid Components /15./. Český Krumlov (CZ), 05.06.2011-10.06.2011]
R&D Projects: GA MŠMT LC512; GA ČR GA203/09/0317; GA MŠMT 1M0508; GA AV ČR(CZ) IAA400040901
Institutional research plan: CEZ:AV0Z40550506
Keywords : nucleosides * anthraquinone * DNA
Subject RIV: CC - Organic Chemistry

Modified 2′-deoxynucleosides and nucleoside triphosphates (dNTPs) bearing anthraquinone (AQ) via acetylene or propargylcarbamoyl linkers were prepared by single-step Sonogashira cross-coupling reactions halogenated nucleosides (7-iodo-7-deaza-2′-deoxyadenosine and 5-iodo-2′-deoxycytidine) or dNTPs with N-(2-propynyl)-anthraquinone carboxamide and 2-ethynylantraquinone. Polymerase incorporation of the AQ-labelled dNTPs into DNA has also been studied. Square-wave voltammetry of the AQ-labelled nucleosides and nucleotides showed one reversible peak at –0.5 V.
Permanent Link: http://hdl.handle.net/11104/0198836