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

J 2012

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

RAINDLOVA, Veronika, Radek POHL, Blanka KLEPETAROVA, Luděk HAVRAN, Eva SIMKOVA et. al.

Basic information

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10610 Biophysics

Country of publisher

Germany

Confidentiality degree

není předmětem státního či obchodního tajemství

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

Abstract

V originále

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.

Citovat

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.

@article{1179811,
   author = {Raindlova, Veronika and Pohl, Radek and Klepetarova, Blanka and Havran, Luděk and Simkova, Eva and Horakova, Petra and Pivoňková, Hana and Fojta, Miroslav and Hocek, Michal},
   article_location = {Weinheim},
   article_number = {8},
   doi = {http://dx.doi.org/10.1002/cplu.201200056},
   keywords = {cross-coupling; DNA; electrochemistry; hydrazones; nucleotides; polymerases},
   language = {eng},
   issn = {2192-6506},
   journal = {CHEMPLUSCHEM},
   title = {Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling},
   volume = {77},
   year = {2012}
}

TY  - JOUR
ID  - 1179811
AU  - Raindlova, Veronika - Pohl, Radek - Klepetarova, Blanka - Havran, Luděk - Simkova, Eva - Horakova, Petra - Pivoňková, Hana - Fojta, Miroslav - Hocek, Michal
PY  - 2012
TI  - Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling
JF  - CHEMPLUSCHEM
VL  - 77
IS  - 8
SP  - 652-662
EP  - 652-662
PB  - Wiley - Verlag Chemie
SN  - 21926506
KW  - cross-coupling
KW  - DNA
KW  - electrochemistry
KW  - hydrazones
KW  - nucleotides
KW  - polymerases
N2  - 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.
ER  -

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. \textit{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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