title: Synthesis and oligomerization of Fmoc/Boc-protected PNA monomers of 2,6-diaminopurine, 2-aminopurine and thymine.
abstract: A Boc-protecting group strategy for Fmoc-based PNA (peptide nucleic acid) oligomerization has been developed for thymine, 2,6-diaminopurine (DAP) and 2-aminopurine (2AP). The monomers may be used interchangeably with standard Fmoc PNA monomers. The DAP monomer was incorporated into a PNA and was found to selectively bind to T (ΔT(m)≥ +6 °C) in a complementary DNA strand. The 2AP monomer showed excellent discrimination of T (ΔT(m)≥ +12 °C) over the other nucleobases. 2AP also acted as a fluorescent probe of the PNA:DNA duplexes and displayed fluorescence quenching dependent on the opposite base.
authors.affiliation: Department of Chemistry, University of Western Ontario, London, Canada.
authors.forename: André H
authors.initials: AH
authors.lastname: St Amant
authors.forename: Robert H E
authors.initials: RH
authors.lastname: Hudson
mesh_terms: D015075:2-Aminopurine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D004247:DNA / Q000378:metabolism; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013050:Spectrometry, Fluorescence; D013941:Thymine / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism
chemical_list: D020135:Peptide Nucleic Acids; D015075:2-Aminopurine; C007300:2,6-diaminopurine; D004247:DNA; D013941:Thymine