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.

Základní údaje

Originální název

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

Autoři

RAINDLOVA, Veronika (203 Česká republika), Radek POHL (203 Česká republika), Blanka KLEPETAROVA (203 Česká republika), Luděk HAVRAN (203 Česká republika), Eva SIMKOVA (203 Česká republika), Petra HORAKOVA (203 Česká republika), Hana PIVOŇKOVÁ (203 Česká republika), Miroslav FOJTA (203 Česká republika, garant, domácí) a Michal HOCEK (203 Česká republika)

Vydání

CHEMPLUSCHEM, Weinheim, Wiley - Verlag Chemie, 2012, 2192-6506

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10610 Biophysics

Stát vydavatele

Německo

Utajení

není předmětem státního či obchodního tajemství

Kód RIV

RIV/00216224:14740/12:00073028

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1002/cplu.201200056

UT WoS

000307401800006

Klíčová slova anglicky

cross-coupling; DNA; electrochemistry; hydrazones; nucleotides; polymerases

Štítky

ok, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 25. 4. 2014 17:38, Olga Křížová

Anotace

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 a Michal HOCEK. Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling. CHEMPLUSCHEM. Weinheim: Wiley - Verlag Chemie, 2012, roč. 77, č. 8, s. 652-662. ISSN 2192-6506. Dostupné z: 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 a Michal HOCEK. Synthesis of Hydrazone-Modified Nucleotides and Their Polymerase Incorporation onto DNA for Redox Labeling. \textit{CHEMPLUSCHEM}. Weinheim: Wiley - Verlag Chemie, 2012, roč.~77, č.~8, s.~652-662. ISSN~2192-6506. Dostupné z: https://dx.doi.org/10.1002/cplu.201200056.

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