title: PNA Molecular Beacons Assembled by Post-Synthetic Click Chemistry Functionalization.
abstract: To avoid the tedious synthesis of functionalized peptide nucleic acid (PNA) monomers for probe development, we proposed a simple approach to modify PNA oligomers by post-synthetic on-resin click chemistry. PNA molecular beacons (MBs) were prepared by incorporation of azide-containing monomers into the oligomer by automatic solid-phase peptide synthesis and subsequent derivatization with pyrene moieties by copper-catalyzed azide-alkyne cycloaddition. Two pyrene-based quencher-free PNA molecular beacons, a stemless MB and one possessing a stem-loop structure, targeting a portion of the cystic fibrosis gene, were successfully synthesized by using this method. Fluorescence studies showed that the stem-loop MB exhibited better discrimination of changes in excimer/monomer ratios as compared to the stemless MB construct.
authors.affiliation: Department of Chemistry, The University of Western Ontario, 1151 Richmond Street, London, ON, N6A 2K5, Canada.
authors.forename: Xiaoxiao
authors.initials: X
authors.lastname: Wang
authors.affiliation: Department of Chemistry, The University of Western Ontario, 1151 Richmond Street, London, ON, N6A 2K5, Canada. robert.hudson@uwo.ca.
authors.forename: Robert H E
authors.initials: RH
authors.lastname: Hudson
mesh_terms: D001386:Azides / Q000737:chemistry; D057930:Click Chemistry; D005453:Fluorescence; D015394:Molecular Structure; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013050:Spectrometry, Fluorescence
chemical_list: D001386:Azides; D020135:Peptide Nucleic Acids
keywords: click chemistry; molecular beacon; peptide nucleic acids; post-synthetic modification; pyrene fluorescent probe