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2-Allyl- and Propargylamino-dATPs for Site-Specific Enzymatic Introduction of a Single Modification in the Minor Groove of DNA
- 1.0495370 - ÚOCHB 2019 RIV DE eng J - Journal Article
Matyašovský, Ján - Pohl, Radek - Hocek, Michal
2-Allyl- and Propargylamino-dATPs for Site-Specific Enzymatic Introduction of a Single Modification in the Minor Groove of DNA.
Chemistry - A European Journal. Roč. 24, č. 56 (2018), s. 14938-14941. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR(CZ) GA17-03419S; GA ČR(CZ) GA18-03305S; GA MŠMT(CZ) EF16_019/0000729
EU Projects: European Commission(XE) 642023 - ClickGene
Grant - others:AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963
Keywords : DNA * fluorescent probes * nucleotides * oligonucleotides * polymerases
OECD category: Organic chemistry
Impact factor: 5.160, year: 2018
https://onlinelibrary.wiley.com/doi/full/10.1002/chem.201803973
A series of 2-alkylamino-2-deoxyadenosine triphosphates (dATP) was prepared and found to be substrates for the Therminator DNA polymerase, which incorporated only one modified nucleotide into the primer. Using a template encoding for two consecutive adenines, conditions were found for incorporation of either one or two modified nucleotides. In all cases, addition of a mixture of natural dNTPs led to primer extension resulting in site-specific single modification of DNA in the minor groove. The allylamino-substituted DNA was used for the thiol-ene addition, whereas the propargylamino-DNA for the CuAAC click reaction was used to label the DNA with a fluorescent dye in the minor groove. The approach was used to construct FRET probes for detection of oligonucleotides.
Permanent Link: http://hdl.handle.net/11104/0288398
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