5-(Pyren-1-yl)uracil as a Base-Discriminating Fluorescent Nucleobase in Pyrrolidinyl Peptide Nucleic Acids

Boonlua, Chalothorn and Vilaivan, Chotima and Wagenknecht, Hans-Achim and Vilaivan, Tirayut (2011) 5-(Pyren-1-yl)uracil as a Base-Discriminating Fluorescent Nucleobase in Pyrrolidinyl Peptide Nucleic Acids. CHEMISTRY-AN ASIAN JOURNAL, 6 (12). pp. 3251-3259. ISSN 1861-4728,

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Abstract

A pyrene-labeled uridine (UPy) monomer for a pyrrolidinyl peptide nucleic acid with an alternating proline/2-aminocyclopentanecarboxylic acid backbone (acpcPNA) was synthesized and incorporated into the PNA. The UPy base in acpcPNA could specifically recognize the base A in its complementary DNA strand as determined by thermal denaturation (Tm) experiments. The fluorescence of the UPy-containing single-stranded acpcPNA was very weak in aqueous buffer. In the presence of a complementary DNA target, the fluorescence was enhanced significantly (2.741.9 folds, depending on sequences). The fluorescence enhancement was specific to the pairing between UPy and dA, making the UPy-modified acpcPNA useful as a hybridization-responsive fluorescence probe for DNA-sequence determination.

Item Type: Article
Uncontrolled Keywords: ELECTRON-TRANSFER; OLIGONUCLEOTIDE PROBES; MOLECULAR BEACON; DNA; NUCLEOSIDES; HYBRIDIZATION; PHOTOPHYSICS; DISTINCTION; CYTOSINE; ANALOGS; electron transfer; fluorescence; molecular beacons; oligonucleotides; peptide nucleic acids
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Alumni or Retired Professors > Arbeitskreis Prof. Dr. Hans-Achim Wagenknecht
Depositing User: Dr. Gernot Deinzer
Date Deposited: 25 May 2020 13:04
Last Modified: 25 May 2020 13:04
URI: https://pred.uni-regensburg.de/id/eprint/19683

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