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5‐(Pyren‐1‐yl)uracil as a Base‐Discriminating Fluorescent Nucleobase in Pyrrolidinyl Peptide Nucleic Acids
Author(s) -
Boonlua Chalothorn,
Vilaivan Chotima,
Wagenknecht HansAchim,
Vilaivan Tirayut
Publication year - 2011
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201100490
Subject(s) - nucleic acid , fluorescence , peptide nucleic acid , nucleobase , dna , chemistry , pyrene , uracil , monomer , base pair , peptide , nucleic acid thermodynamics , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , polymer , base sequence , physics , quantum mechanics
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.