Clickable peptide nucleic acids (cPNA) with tunable affinity

被引:20
作者
Chouikhi, Dalila [1 ]
Barluenga, Sofia [1 ]
Winssinger, Nicolas [1 ]
机构
[1] Univ Strasbourg, ISIS, UMR 7006, CNRS, F-67000 Strasbourg, France
基金
欧洲研究理事会;
关键词
AZIDE-ALKYNE CYCLOADDITION; TERMINAL ALKYNES; PNA SYNTHESIS; SOLID-PHASE; DNA; LIGATION; OLIGONUCLEOTIDES; AMPLIFICATION; MICROARRAYS; CHEMISTRY;
D O I
10.1039/c0cc01081b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Peptide nucleic acids (PNAs) are functional analogues of natural oligonucleotides. Herein, we report the synthesis of PNAs bearing a triazole in lieu of the amide bond assembled using a "click" cycloaddition, their hybridization properties as well as the DNA-templated coupling of the azide and alkyne PNA fragments.
引用
收藏
页码:5476 / 5478
页数:3
相关论文
共 33 条
[1]   Peptidomimetics via copper-catalyzed azide-alkyne cycloadditions [J].
Angell, Yu L. ;
Burgess, Kevin .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (10) :1674-1689
[2]  
Brudno Y, 2010, NAT CHEM BIOL, V6, P148, DOI [10.1038/nchembio.280, 10.1038/NCHEMBIO.280]
[3]   Azidopeptide nucleic acid. An alternative strategy for solid-phase peptide nucleic acid (PNA) synthesis [J].
Debaene, F ;
Winssinger, N .
ORGANIC LETTERS, 2003, 5 (23) :4445-4447
[4]   Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metalloproteases as well as tyrosine phosphatases [J].
Debaene, Francois ;
Da Silva, Julien A. ;
Pianowski, Zbigniew ;
Duran, Fernando J. ;
Winssinger, Nicolas .
TETRAHEDRON, 2007, 63 (28) :6577-6586
[5]   Single nucleotide specific detection of DNA by native chemical ligation of fluorescence labeled PNA-probes [J].
Dose, Christian ;
Seitz, Oliver .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (01) :65-77
[6]   PNA HYBRIDIZES TO COMPLEMENTARY OLIGONUCLEOTIDES OBEYING THE WATSON-CRICK HYDROGEN-BONDING RULES [J].
EGHOLM, M ;
BUCHARDT, O ;
CHRISTENSEN, L ;
BEHRENS, C ;
FREIER, SM ;
DRIVER, DA ;
BERG, RH ;
KIM, SK ;
NORDEN, B ;
NIELSEN, PE .
NATURE, 1993, 365 (6446) :566-568
[7]   Synthesis and Polymerase Chain Reaction Amplification of DNA Strands Containing an Unnatural Triazole Linkage [J].
El-Sagheer, Afaf H. ;
Brown, Tom .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (11) :3958-3964
[8]   Single-nucleotide-specific PNA-peptide ligation on synthetic and PCR DNA templates [J].
Ficht, S ;
Mattes, A ;
Seitz, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (32) :9970-9981
[9]   PNA encoding (PNA = peptide nucleic acid): From solution-based libraries to organized microarrays [J].
Harris, JL ;
Winssinger, N .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (23) :6792-6801
[10]   Analysis and Optimization of Copper-Catalyzed Azide-Alkyne Cycloaddition for Bioconjugation [J].
Hong, Vu ;
Presolski, Stanislav I. ;
Ma, Celia ;
Finn, M. G. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9879-9883