title: 5-(Pyren-1-yl)uracil as a base-discriminating fluorescent nucleobase in pyrrolidinyl peptide nucleic acids.
abstract: A pyrene-labeled uridine (U(Py)) monomer for a pyrrolidinyl peptide nucleic acid with an alternating proline/2-aminocyclopentanecarboxylic acid backbone (acpcPNA) was synthesized and incorporated into the PNA. The U(Py) base in acpcPNA could specifically recognize the base A in its complementary DNA strand as determined by thermal denaturation (T(m)) experiments. The fluorescence of the U(Py)-containing single-stranded acpcPNA was very weak in aqueous buffer. In the presence of a complementary DNA target, the fluorescence was enhanced significantly (2.7-41.9 folds, depending on sequences). The fluorescence enhancement was specific to the pairing between U(Py) and dA, making the U(Py)-modified acpcPNA useful as a hybridization-responsive fluorescence probe for DNA-sequence determination.
authors: Organic Synthesis Research Unit, Department of Chemistry, Faculty of Science, Chulalongkorn University, Phayathai Road, Patumwan, Bangkok 10330, Thailand.
authors: Chalothorn
authors: C
authors: Boonlua
authors: Chotima
authors: C
authors: Vilaivan
authors: Hans-Achim
authors: HA
authors: Wagenknecht
authors: Tirayut
authors: T
authors: Vilaivan
mesh_terms: D009693:Nucleic Acid Hybridization; D020135:Peptide Nucleic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D011721:Pyrenes / Q000737:chemistry*; D011789:Quantum Theory; D013056:Spectrophotometry, Ultraviolet; D044366:Transition Temperature; D014498:Uracil / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: C570985:5-(pyren-1-yl)uracil; D020135:Peptide Nucleic Acids; D011721:Pyrenes; D014498:Uracil; C030984:pyrene