title: Synthesis and hybridization properties of DNA-PNA chimeras carrying 5-bromouracil and 5-methylcytosine.
abstract: The preparation of 5-bromouracil and 5-methylcytosine peptide nucleic acid (PNA) monomers is described. These PNA monomers were used for the preparation of several DNA-PNA chimeras and their hybridization properties are described. The substitution of cytosine by 5-methylcytosine in DNA-PNA chimeras increased duplex stability while substitution of thymine by 5-bromouracil maintained it. Moreover, binding of DNA-PNA chimeras to double-stranded DNA to form triple helices was studied. In contrast to DNA, the presence of 5-methylcytosine and 5-bromouracil in DNA-PNA chimeras destabilized triple helix.
authors.affiliation: European Molecular Biology Laboratory, Heidelberg, Germany.
authors.forename: E
authors.initials: E
authors.lastname: Ferrer
authors.forename: A
authors.initials: A
authors.lastname: Shevchenko
authors.forename: R
authors.initials: R
authors.lastname: Eritja
mesh_terms: D044503:5-Methylcytosine; D001483:Base Sequence; D001976:Bromouracil / Q000737:chemistry*; D003596:Cytosine / Q000031:analogs & derivatives* / Q000737:chemistry; D004247:DNA / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009693:Nucleic Acid Hybridization; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D020135:Peptide Nucleic Acids; D001976:Bromouracil; D044503:5-Methylcytosine; D003596:Cytosine; D004247:DNA