Butylacrylate-nucleobase Conjugates as Targets for Two-step Redox Labeling of DNA with an Osmium Tetroxide Complex

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00488410" target="_blank" >RIV/61388963:_____/18:00488410 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/68081707:_____/18:00488410 RIV/00216224:14740/18:00104757 RIV/00216208:11310/18:10374846

Výsledek na webu

<a href="http://dx.doi.org/10.1002/elan.201700702" target="_blank" >http://dx.doi.org/10.1002/elan.201700702</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/elan.201700702" target="_blank" >10.1002/elan.201700702</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Butylacrylate-nucleobase Conjugates as Targets for Two-step Redox Labeling of DNA with an Osmium Tetroxide Complex

Popis výsledku v původním jazyce

Modification of nucleic acids with osmium tetroxide reagents (Os,L, such as OsO4,2,2-bipyridine, Os,bpy) has been applied in redox DNA labeling, in probing DNA structure as well as in studies of DNA interactions with other molecules. In natural DNA, primarily thymine residues form adducts with the Os,bpy in a structure selective manner. In this paper we introduce a new two-step technique of DNA modification with the electroactive Os,bpy, consisting in enzymatic construction of DNA bearing butyl acrylate (BA) moieties attached to uracil at C5 or to 7-deaza adenine at C7, followed by chemical modification of a reactive C=C double bond in the acrylate residue. We demonstrate a facile modification of the BA conjugates in both single- and double-stranded (ds) DNA under conditions when modification within the nucleobase rings in ds DNA is hindered. Various DNA-Os,bpy adducts can easily be analyzed electrochemically and distinguished by different redox potentials. The two-step procedure appears to be applicable in osmium redox labelling of ds DNA.

Název v anglickém jazyce

Butylacrylate-nucleobase Conjugates as Targets for Two-step Redox Labeling of DNA with an Osmium Tetroxide Complex

Popis výsledku anglicky

Modification of nucleic acids with osmium tetroxide reagents (Os,L, such as OsO4,2,2-bipyridine, Os,bpy) has been applied in redox DNA labeling, in probing DNA structure as well as in studies of DNA interactions with other molecules. In natural DNA, primarily thymine residues form adducts with the Os,bpy in a structure selective manner. In this paper we introduce a new two-step technique of DNA modification with the electroactive Os,bpy, consisting in enzymatic construction of DNA bearing butyl acrylate (BA) moieties attached to uracil at C5 or to 7-deaza adenine at C7, followed by chemical modification of a reactive C=C double bond in the acrylate residue. We demonstrate a facile modification of the BA conjugates in both single- and double-stranded (ds) DNA under conditions when modification within the nucleobase rings in ds DNA is hindered. Various DNA-Os,bpy adducts can easily be analyzed electrochemically and distinguished by different redox potentials. The two-step procedure appears to be applicable in osmium redox labelling of ds DNA.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

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OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA15-08434S" target="_blank" >GA15-08434S: Nové reaktivní skupiny zavedené do nukleových kyselin pro modifikaci oxokomplexy osmia: strukturní a analytické aspekty</a><br>

Návaznosti

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

Rok uplatnění

2018

Kód důvěrnosti údajů

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

Název periodika

Electroanalysis

ISSN

1040-0397

e-ISSN

—

Svazek periodika

30

Číslo periodika v rámci svazku

2

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

7

Strana od-do

371-377

Kód UT WoS článku

000424874800024

EID výsledku v databázi Scopus

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