2-Allyl- and Propargylamino-dATPs for Site-Specific Enzymatic Introduction of a Single Modification in the Minor Groove of DNA

0495370 - ÚOCHB 2019 RIV DE eng J - Článek v odborném periodiku
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
Grant CEP: GA ČR(CZ) GA17-03419S; GA ČR(CZ) GA18-03305S; GA MŠMT(CZ) EF16_019/0000729
GRANT EU: European Commission(XE) 642023 - ClickGene
Grant ostatní: AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institucionální podpora: RVO:61388963
Klíčová slova: DNA * fluorescent probes * nucleotides * oligonucleotides * polymerases
Obor OECD: Organic chemistry
Impakt faktor: 5.160, rok: 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.
Trvalý link: http://hdl.handle.net/11104/0288398