Additions of Thiols to 7-Vinyl-7-deazaadenine Nucleosides and Nucleotides. Synthesis of Hydrophobic Derivatives of 2'-Deoxyadenosine, dATP and DNA

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F16%3A00470348" target="_blank" >RIV/61388963:_____/16:00470348 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/16:10330304

Výsledek na webu

<a href="http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02098" target="_blank" >http://pubs.acs.org/doi/abs/10.1021/acs.joc.6b02098</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.joc.6b02098" target="_blank" >10.1021/acs.joc.6b02098</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Additions of Thiols to 7-Vinyl-7-deazaadenine Nucleosides and Nucleotides. Synthesis of Hydrophobic Derivatives of 2'-Deoxyadenosine, dATP and DNA

Popis výsledku v původním jazyce

Additions of alkyl-or arylthiols to 7-vinyl-7-deaza2'-deoxyadenosine gave a series of 7-[2-(alkyl-or arylsulfanyl)ethyl]-7-deaza-2'-deoxyadenosines in 45-85% yields. The nucleosides were converted to 5'-0-mono-(dA(SR)MP) or triphosphates (dA(SR)TP) by phosphorylation. The modified triphosphates were also prepared by thiol addition to 7-vinyl-7deaza-dATP. The triphosphates dASRTP were good substrates for DNA polymerases useful in the enzymatic synthesis of base-modified oligonucleotides (ONs) or DNA containing flexibly linked hydrophobic substituents in the major groove. Primer extension was used for the synthesis of ONs with one or several modifications, PCR was used for the synthesis of heavily modified DNA, whereas terminal deoxynucleotidyl transferase was used for a single-nucleotide labeling of the 3'-end.

Název v anglickém jazyce

Additions of Thiols to 7-Vinyl-7-deazaadenine Nucleosides and Nucleotides. Synthesis of Hydrophobic Derivatives of 2'-Deoxyadenosine, dATP and DNA

Popis výsledku anglicky

Additions of alkyl-or arylthiols to 7-vinyl-7-deaza2'-deoxyadenosine gave a series of 7-[2-(alkyl-or arylsulfanyl)ethyl]-7-deaza-2'-deoxyadenosines in 45-85% yields. The nucleosides were converted to 5'-0-mono-(dA(SR)MP) or triphosphates (dA(SR)TP) by phosphorylation. The modified triphosphates were also prepared by thiol addition to 7-vinyl-7deaza-dATP. The triphosphates dASRTP were good substrates for DNA polymerases useful in the enzymatic synthesis of base-modified oligonucleotides (ONs) or DNA containing flexibly linked hydrophobic substituents in the major groove. Primer extension was used for the synthesis of ONs with one or several modifications, PCR was used for the synthesis of heavily modified DNA, whereas terminal deoxynucleotidyl transferase was used for a single-nucleotide labeling of the 3'-end.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

—

Projekt

<a href="/cs/project/GA14-04289S" target="_blank" >GA14-04289S: Modifikace a bioorthogonální reakce ve velkém žlábku DNA pro regulaci vazby proteinů a genové exprese</a><br>

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2016

Kód důvěrnosti údajů

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

Název periodika

Journal of Organic Chemistry

ISSN

0022-3263

e-ISSN

—

Svazek periodika

81

Číslo periodika v rámci svazku

22

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

11

Strana od-do

11115-11125

Kód UT WoS článku

000391248800048

EID výsledku v databázi Scopus

2-s2.0-84996560182