Fast copper-free click DNA ligation by the ring-strain promoted alkyne-azide cycloaddition reaction

被引:86
作者
Shelbourne, Montserrat [1 ]
Chen, Xiong [1 ]
Brown, Tom [1 ]
El-Sagheer, Afaf H. [1 ,2 ]
机构
[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England
[2] Suez Canal Univ, Chem Branch, Dept Sci & Math, Fac Petr & Min Engn, Suez 43721, Egypt
关键词
SIDE-CHAINS; CHEMISTRY; FUNCTIONALIZATION; HAIRPIN; GLYCANS; (TL)DNA; ANALOG;
D O I
10.1039/c1cc10743g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Templated DNA strand ligation by the ring-strain promoted alkyne-azide [3+2] cycloaddition reaction is very fast; with dibenzocyclooctyne, the reaction is essentially complete in 1 min. It is inhibited by the presence of a single mismatched base pair suggesting applications in genetic analysis.
引用
收藏
页码:6257 / 6259
页数:3
相关论文
共 30 条
[1]   Chemical Approaches To Perturb, Profile, and Perceive Glycans [J].
Agard, Nicholas J. ;
Bertozzi, Carolyn R. .
ACCOUNTS OF CHEMICAL RESEARCH, 2009, 42 (06) :788-797
[2]   Comparison of a Nucleosidic vs Non-Nucleosidic Postsynthetic "Click" Modification of DNA with Base-Labile Fluorescent Probes [J].
Berndl, Sina ;
Herzig, Nadine ;
Kele, Peter ;
Lachmann, Daniel ;
Li, Xiaohua ;
Wolfbeis, Otto S. ;
Wagenknecht, Hans-Achim .
BIOCONJUGATE CHEMISTRY, 2009, 20 (03) :558-564
[3]   Copper-free click chemistry in living animals [J].
Chang, Pamela V. ;
Prescher, Jennifer A. ;
Sletten, Ellen M. ;
Baskin, Jeremy M. ;
Miller, Isaac A. ;
Agard, Nicholas J. ;
Lo, Anderson ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (05) :1821-1826
[4]   Azide: A Unique Dipole for Metal-Free Bioorthogonal Ligations [J].
Debets, Marjoke F. ;
van der Doelen, Christianus W. J. ;
Rutjes, Floris P. J. T. ;
van Delft, Floris L. .
CHEMBIOCHEM, 2010, 11 (09) :1168-1184
[5]   A very stable cyclic DNA miniduplex with just two base pairs [J].
El-Sagheer, Afaf H. ;
Kumar, Ravindra ;
Findlow, Stuart ;
Werner, Joern M. ;
Lane, Andrew N. ;
Brown, Tom .
CHEMBIOCHEM, 2008, 9 (01) :50-52
[6]   Rapid chemical ligation of oligonucleotides by the Diels-Alder reaction [J].
El-Sagheer, Afaf H. ;
Cheong, Vee Vee ;
Brown, Tom .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (01) :232-235
[7]   New strategy for the synthesis of chemically modified RNA constructs exemplified by hairpin and hammerhead ribozymes [J].
El-Sagheer, Afaf H. ;
Brown, Tom .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2010, 107 (35) :15329-15334
[8]   Factors influencing hairpin oligonucleotide cyclization by the uncatalyzed alkyne-azide cycloaddition (AAC) reaction [J].
El-Sagheer, Afaf H. ;
Brown, Tom .
PURE AND APPLIED CHEMISTRY, 2010, 82 (08) :1599-1607
[9]   Click chemistry with DNA [J].
El-Sagheer, Afaf H. ;
Brown, Tom .
CHEMICAL SOCIETY REVIEWS, 2010, 39 (04) :1388-1405
[10]   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