Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F21%3A00542459" target="_blank" >RIV/61388963:_____/21:00542459 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/68081707:_____/21:00542459 RIV/00216208:11310/21:10428478

Výsledek na webu

<a href="https://doi.org/10.1021/jacs.1c02222" target="_blank" >https://doi.org/10.1021/jacs.1c02222</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/jacs.1c02222" target="_blank" >10.1021/jacs.1c02222</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing

Popis výsledku v původním jazyce

We report a series of 2′-deoxyribonucleoside triphosphates bearing dicarba-nido-undecaborate ([C2B9H11]1–), [3,3′-iron-bis(1,2-dicarbollide)]− (FESAN, [Fe(C2B9H11)2]2–) or [3,3′-cobalt-bis(1,2-dicarbollide)]− (COSAN, [Co(C2B9H11)2]2–) groups prepared either through the Sonogashira cross-coupling or the CuAAC click reaction. The modified dNXTPs were substrates for KOD XL DNA polymerase in enzymatic synthesis of modified DNA through primer extension (PEX). The nido-carborane- and FESAN-modified nucleotides gave analytically useful oxidation signals in square-wave voltammetry and were used for redox labeling of DNA. The redox-modified DNA probes were prepared by PEX using tailed primers and were hybridized to electrode (gold or glassy carbon) containing capture oligonucleotides. The combination of nido-carborane- and FESAN-linked nucleotides with 7-ferrocenylethynyl-7-deaza-dATP and 7-deaza-dGTP allowed polymerase synthesis of DNA fully modified at all four nucleobases, and each of the redox labels gave four differentiable and ratiometric signals in voltammetry. Thus, the combination of these four redox labels constitutes the first fully orthogonal redox coding of all four canonical nucleobases, which can be used for determination of nucleobase composition of short DNA stretches in one simple PEX experiment with electrochemical readout.

Název v anglickém jazyce

Carborane- or Metallacarborane-Linked Nucleotides for Redox Labeling. Orthogonal Multipotential Coding of all Four DNA Bases for Electrochemical Analysis and Sequencing

Popis výsledku anglicky

We report a series of 2′-deoxyribonucleoside triphosphates bearing dicarba-nido-undecaborate ([C2B9H11]1–), [3,3′-iron-bis(1,2-dicarbollide)]− (FESAN, [Fe(C2B9H11)2]2–) or [3,3′-cobalt-bis(1,2-dicarbollide)]− (COSAN, [Co(C2B9H11)2]2–) groups prepared either through the Sonogashira cross-coupling or the CuAAC click reaction. The modified dNXTPs were substrates for KOD XL DNA polymerase in enzymatic synthesis of modified DNA through primer extension (PEX). The nido-carborane- and FESAN-modified nucleotides gave analytically useful oxidation signals in square-wave voltammetry and were used for redox labeling of DNA. The redox-modified DNA probes were prepared by PEX using tailed primers and were hybridized to electrode (gold or glassy carbon) containing capture oligonucleotides. The combination of nido-carborane- and FESAN-linked nucleotides with 7-ferrocenylethynyl-7-deaza-dATP and 7-deaza-dGTP allowed polymerase synthesis of DNA fully modified at all four nucleobases, and each of the redox labels gave four differentiable and ratiometric signals in voltammetry. Thus, the combination of these four redox labels constitutes the first fully orthogonal redox coding of all four canonical nucleobases, which can be used for determination of nucleobase composition of short DNA stretches in one simple PEX experiment with electrochemical readout.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2021

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Journal of the American Chemical Society

ISSN

0002-7863

e-ISSN

1520-5126

Svazek periodika

143

Číslo periodika v rámci svazku

18

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

11

Strana od-do

7124-7134

Kód UT WoS článku

000651748000044

EID výsledku v databázi Scopus

2-s2.0-85106466637