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

被引：27

作者：

Boonlua, Chalothorn ^{[3
]}

Vilaivan, Chotima ^{[3
]}

Wagenknecht, Hans-Achim ^{[1
,2
]}

Vilaivan, Tirayut ^{[3
]}

机构：

[1] Karlsruhe Inst Technol, Inst Organ Chem, D-76131 Karlsruhe, Germany

[2] Univ Regensburg, Inst Organ Chem, D-93040 Regensburg, Germany

[3] Chulalongkorn Univ, Fac Sci, Dept Chem, Organ Synth Res Unit, Bangkok 10330, Thailand

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2011年 / 6卷 / 12期

关键词：

electron transfer; fluorescence; molecular beacons; oligonucleotides; peptide nucleic acids; ELECTRON-TRANSFER; OLIGONUCLEOTIDE PROBES; MOLECULAR BEACON; DNA; NUCLEOSIDES; HYBRIDIZATION; PHOTOPHYSICS; DISTINCTION; CYTOSINE; ANALOGS;

D O I：

10.1002/asia.201100490

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：3251 / 3259

页数：9

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