6-Aryl-4-amino-pyrimido[4,5-b]indole 2'-deoxyribonucleoside triphosphates (benzo-fused 7-deaza-dATP analogues): Synthesis, fluorescent properties, enzymatic incorporation into DNA and DNA-protein binding study

0464456 - ÚOCHB 2017 RIV GB eng J - Journal Article
Bosáková, A. - Perlíková, Pavla - Tichý, Michal - Pohl, Radek - Hocek, Michal
6-Aryl-4-amino-pyrimido[4,5-b]indole 2'-deoxyribonucleoside triphosphates (benzo-fused 7-deaza-dATP analogues): Synthesis, fluorescent properties, enzymatic incorporation into DNA and DNA-protein binding study.
Bioorganic & Medicinal Chemistry. Roč. 24, č. 19 (2016), s. 4528-4535. ISSN 0968-0896. E-ISSN 1464-3391
R&D Projects: GA ČR(CZ) GA16-00178S
Institutional support: RVO:61388963
Keywords : nucleosides * nucleotides * pyrimidoindoles * deazapurines * fluorescence * DNA polymerase
Subject RIV: CC - Organic Chemistry
Impact factor: 2.930, year: 2016

Four 6-substituted 4-amino-pyrimido[4,5-b]indole 2'-deoxyribonucleoside triphosphates (dA(BX)TPs) were prepared by glycosylation of 4,6-dichloropyrimidoindole followed by ammonolysis, cross-coupling and triphosphorylation. They were found to be moderate to good substrates for DNA polymerases in primer extension. They also exerted fluorescence with emission maxima 335-378 nm. When incorporated to oligonucleotide probes, they did not show significant mismatch discrimination but the 6-benzofuryl 4-amino-pyrimido[4,5-b]indole nucleotide displayed a useful sensitivity to protein binding in experiment with SSB protein.
Permanent Link: http://hdl.handle.net/11104/0263311