Synthesis of Fluorine-Labeled Peptide Nucleic Acid Building Blocks as Sensors for the 19F NMR Spectroscopic Detection of Different Hybridization Modes



: Anu Kiviniemi, Merita Murtola, Petri Ingman, and Pasi Virta

Publisher: AMER CHEMICAL SOC

: 2013

: Journal of Organic Chemistry

: JOURNAL OF ORGANIC CHEMISTRY

: J ORG CHEM

: 11

: 78

: 11

: 5153

: 5159

: 7

: 0022-3263

DOI: https://doi.org/10.1021/jo400014y


Peptide nucleic acid (PNA) building blocks, bearing a fluorine sensor at C-5 of the uracil base [viz. trifluoromethyl and 3,3-bis(trifluoromethyl)-4,4,4-trifluorobut-1-ynyl], were synthesized and incorporated to a PNA strand, and their applicability for the monitoring of different hybridization modes by F-19 NMR spectroscopy was studied. Both sensors gave unique F-19 resonance shifts in NMR when the PNA was targeted to a complementary antiparallel DNA, antiparallel RNA, parallel DNA, and parallel RNA. The 5-trifluoromethyl-derived sensor was additionally applied for the monitoring of interconversions from a parallel DNA/PNA complex to an antiparallel RNA/PNA complex and from a PNA/PNA complex to two DNA/PNA complexes (i.e., double-duplex invasion).



Last updated on 2024-26-11 at 15:43