title: A solid-phase CuAAC strategy for the synthesis of PNA containing nucleobase surrogates.
abstract: The synthesis of an azide containing PNA monomer is described. The monomer was incorporated into two PNA sequences for the purpose of synthesizing an intercalating fluorophore-labeled PNA and a metal binding hairpin using a solid phase copper catalyzed azide-alkyne Huisgen cycloaddition (CuAAC). Click chemistry was performed using 2-ethynylfluorene or 1-ethynylpyrene to add a fluorophore to the PNA, which were tested for their ability to recognize an abasic site on a DNA target. A PNA hairpin possessing azide monomers at each termini was synthesized and reacted with 2-ethynylpyridine to form a hairpin that is stabilized by Ni²⁺.
authors: Department of Chemistry, The University of Western Ontario, London, ON, Canada.
authors: André H
authors: AH
authors: St Amant
authors: Christopher
authors: C
authors: Engbers
authors: Robert H E
authors: RH
authors: Hudson
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D057930:Click Chemistry; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D009690:Nucleic Acid Conformation; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis*
chemical_list: D000480:Alkynes; D001386:Azides; D020135:Peptide Nucleic Acids
keywords: Huisgen cycloaddition; click chemistry; fluorene; hairpin; metal-binding; on-resin; pyrene