Synthesis and Photophysical Properties of Biaryl-Substituted Nucleos(t)ides. Polymerase Synthesis of DNA Probes Bearing Solvatochromic and pH Sensitive Dual Fluorescent and 19F NMR Labels

0377722 - ÚOCHB 2013 RIV US eng J - Journal Article
Riedl, Jan - Pohl, Radek - Rulíšek, Lubomír - Hocek, Michal
Synthesis and Photophysical Properties of Biaryl-Substituted Nucleos(t)ides. Polymerase Synthesis of DNA Probes Bearing Solvatochromic and pH Sensitive Dual Fluorescent and 19F NMR Labels.
Journal of Organic Chemistry. Roč. 77, č. 2 (2012), s. 1026-1044. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA ČR GA203/09/0317
Institutional research plan: CEZ:AV0Z40550506
Keywords : nucleotides * biaryls * fluorescence * DNA
Subject RIV: CC - Organic Chemistry
Impact factor: 4.564, year: 2012

The design of four new fluorinated biaryl fluorescent labels and their attachment to nucleosides and nucleoside triphosphates (dNTPs) by the aqueous cross-coupling reactions of biarylboronates is reported. The modified dNTPs were good substrates for KOD XL polymerase and were enzymatically incorporated into DNA probes. The photophysical properties of the biaryl-modified nucleosides, dNTPs, and DNA were studied systematically. Some labels were used for detection of secondary structure changes, mismatch pairing or pH microenvironment.
Permanent Link: http://hdl.handle.net/11104/0209814