2-Substituted dATP Derivatives as Building Blocks for Polymerase-Catalyzed Synthesis of DNA Modified in the Minor Groove

0469642 - ÚOCHB 2017 RIV DE eng J - Journal Article
Matyašovský, Ján - Perlíková, Pavla - Malnuit, Vincent - Pohl, Radek - Hocek, Michal
2-Substituted dATP Derivatives as Building Blocks for Polymerase-Catalyzed Synthesis of DNA Modified in the Minor Groove.
Angewandte Chemie - International Edition. Roč. 55, č. 51 (2016), s. 15856-15859. ISSN 1433-7851. E-ISSN 1521-3773
R&D Projects: GA ČR GA14-04289S
EU Projects: European Commission(XE) 642023 - ClickGene
Institutional support: RVO:61388963
Keywords : bioconjugation * DNA modification * DNA polymerase * nucleotides * fluorescent labelling
Subject RIV: CC - Organic Chemistry
Impact factor: 11.994, year: 2016
http://onlinelibrary.wiley.com/doi/10.1002/anie.201609007/full

2-Deoxyadenosine triphosphate (dATP) derivatives bearing diverse substituents (Cl, NH2, CH3, vinyl, ethynyl, and phenyl) at position 2 were prepared and tested as substrates for DNA polymerases. The 2-phenyl-dATP was not a substrate for DNA polymerases, but the dATPs bearing smaller substituents were good substrates in primer-extension experiments, producing DNA substituted in the minor groove. The vinyl-modified DNA was applied in thiol-ene addition and the ethynyl-modified DNA was applied in a CuAAC click reaction to form DNA labelled with fluorescent dyes in the minor groove.
Permanent Link: http://hdl.handle.net/11104/0267466