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Synthesis of Hydrazone‐Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling
Author(s) -
Raindlová Veronika,
Pohl Radek,
Klepetářová Blanka,
Havran Luděk,
Šimková Eva,
Horáková Petra,
Pivoňková Hana,
Fojta Miroslav,
Hocek Michal
Publication year - 2012
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.201200056
Subject(s) - hydrazone , chemistry , dna , deoxyribonucleosides , combinatorial chemistry , guanine , primer (cosmetics) , nucleotide , dna polymerase , cytosine , stereochemistry , biochemistry , organic chemistry , gene
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.