Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox ...
RAINDLOVA, Veronika, Radek POHL, Blanka KLEPETAROVA, Luděk HAVRAN, Eva SIMKOVA, Petra HORAKOVA, Hana PIVOŇKOVÁ, Miroslav FOJTA and Michal HOCEK. Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling. CHEMPLUSCHEM. Weinheim: Wiley - Verlag Chemie, 2012, vol. 77, No 8, p. 652-662. ISSN 2192-6506. Available from: https://dx.doi.org/10.1002/cplu.201200056. |
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Original name | Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling |
Authors | RAINDLOVA, Veronika (203 Czech Republic), Radek POHL (203 Czech Republic), Blanka KLEPETAROVA (203 Czech Republic), Luděk HAVRAN (203 Czech Republic), Eva SIMKOVA (203 Czech Republic), Petra HORAKOVA (203 Czech Republic), Hana PIVOŇKOVÁ (203 Czech Republic), Miroslav FOJTA (203 Czech Republic, guarantor, belonging to the institution) and Michal HOCEK (203 Czech Republic). |
Edition | CHEMPLUSCHEM, Weinheim, Wiley - Verlag Chemie, 2012, 2192-6506. |
Other information | |
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Original language | English |
Type of outcome | Article in a journal |
Field of Study | 10610 Biophysics |
Country of publisher | Germany |
Confidentiality degree | is not subject to a state or trade secret |
RIV identification code | RIV/00216224:14740/12:00073028 |
Organization unit | Central European Institute of Technology |
Doi | http://dx.doi.org/10.1002/cplu.201200056 |
UT WoS | 000307401800006 |
Keywords in English | cross-coupling; DNA; electrochemistry; hydrazones; nucleotides; polymerases |
Tags | ok, rivok |
Tags | International impact, Reviewed |
Changed by | Changed by: Olga Křížová, učo 56639. Changed: 25/4/2014 17:38. |
Abstract |
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5-(5-Formylthiophen-2-yl)cytosine, 7-(5-formylthiophen-2-yl)-7-deazaadenosine 2'-deoxyribonucleosides, and their 5'-O-triphosphates (dNTPs) were converted into the 2,4-dinitrophenylhydrazone or nitrobenzofurazanyl. The hydrazone-modified dNTPs were enzymatically incorporated into DNA by polymerase catalyzed primer extension (PEX). This direct incorporation of hydrazone-linked dNTPs was compared to previously reported incorporation of aldehyde-modified dNTPs followed by postsynthetic hydrazone formation on DNA to show that the direct incorporation can be used for incorporation of more hydrazone units, however, cleaner PEX products are formed by incorporation of aldehydes and subsequent reaction with hydrazines. Extensive study of electrochemical behavior of the nitroarylhydrazone-linked nucleosides and DNA was performed confirming the potential utility of the hydrazone, nitroaryl, and benzofurazane groups for redox labeling of DNA. |
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