Additions of Thiols to 7-Vinyl-7-deazaadenine Nucleosides and Nucleotides. Synthesis of Hydrophobic Derivatives of 2'-Deoxyadenosine, dATP and DNA
The result's identifiers
Result code in 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>
Alternative codes found
RIV/00216208:11310/16:10330304
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Additions of Thiols to 7-Vinyl-7-deazaadenine Nucleosides and Nucleotides. Synthesis of Hydrophobic Derivatives of 2'-Deoxyadenosine, dATP and DNA
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GA14-04289S" target="_blank" >GA14-04289S: Modifications and bioorthogonal reactions in the major groove of DNA for regulation of protein binding and gene expression</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
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Volume of the periodical
81
Issue of the periodical within the volume
22
Country of publishing house
US - UNITED STATES
Number of pages
11
Pages from-to
11115-11125
UT code for WoS article
000391248800048
EID of the result in the Scopus database
2-s2.0-84996560182