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Synthesis of Fluorine-Labeled Peptide Nucleic Acid Building Blocks as Sensors for the 19F NMR Spectroscopic Detection of Different Hybridization Modes
Tekijät: Anu Kiviniemi, Merita Murtola, Petri Ingman, and Pasi Virta
Kustantaja: AMER CHEMICAL SOC
Julkaisuvuosi: 2013
Journal: Journal of Organic Chemistry
Tietokannassa oleva lehden nimi: JOURNAL OF ORGANIC CHEMISTRY
Lehden akronyymi: J ORG CHEM
Numero sarjassa: 11
Vuosikerta: 78
Numero: 11
Aloitussivu: 5153
Lopetussivu: 5159
Sivujen määrä: 7
ISSN: 0022-3263
DOI: https://doi.org/10.1021/jo400014y
Tiivistelmä
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).
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).
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