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2-Substituted 2'-deoxyinosine 5'-triphosphates as substrates for polymerase synthesis of minor-groove-modified DNA and effects on restriction endonuclease cleavage
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SYSNO ASEP 0520880 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title 2-Substituted 2'-deoxyinosine 5'-triphosphates as substrates for polymerase synthesis of minor-groove-modified DNA and effects on restriction endonuclease cleavage Author(s) Matyašovský, Ján (UOCHB-X) ORCID, RID
Hocek, Michal (UOCHB-X) RID, ORCIDSource Title Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520
Roč. 18, č. 2 (2020), s. 255-262Number of pages 8 s. Language eng - English Country GB - United Kingdom Keywords 2'-deoxyribonucleoside triphosphates ; nucleoside triphosphates ; primer extension Subject RIV CC - Organic Chemistry OECD category Organic chemistry R&D Projects GA17-03419S GA ČR - Czech Science Foundation (CSF) EF16_019/0000729 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000505592200010 EID SCOPUS 85077402073 DOI 10.1039/c9ob02502b Annotation Five 2-substituted 2'-deoxyinosine triphosphates (d (R) ITP) were synthesized and tested as substrates in enzymatic synthesis of minor-groove base-modified DNA. Only 2-methyl and 2-vinyl derivatives proved to be good substrates for Therminator DNA polymerase, whilst all other d (R) ITPs and other tested DNA polymerases did not give full length products in primer extension. The DNA containing 2-vinylhypoxanthine was then further modified through thiol-ene reactions with thiols. Cross-linking reaction between cysteine-containing minor-groove binding dodecapeptide and DNA proceeded thanks to the proximity effect between thiol and vinyl groups inside the minor groove. 2-Substituted dI (R) TPs and also previously prepared 2-substituted 2'-deoxyadenosine triphosphates (d (R) ATP) were then used for enzymatic synthesis of minor-groove modified DNA to study the effect of minor-groove modifications on cleavage of DNA by type II restriction endonucleases (REs). Although the REs should recognize the sequence through H-bonds in the major groove, some minor-groove modifications also had an inhibiting effect on the cleavage. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2021 Electronic address https://pubs.rsc.org/en/content/articlelanding/2020/OB/C9OB02502B#!divAbstract
Number of the records: 1