Postsynthetic DNA Modification through the Copper-Catalyzed Azide-Alkyne Cycloaddition Reaction

被引:348
作者
Gramlich, Philipp M. E. [1 ,2 ]
Wirges, Christian T. [1 ]
Manetto, Antonio [1 ,2 ]
Carell, Thomas [1 ]
机构
[1] Univ Munich, Dept Chem & Biochem, Ctr Integrat Prot Sci, D-81377 Munich, Germany
[2] BASECLICK GmbH, D-82327 Tutzing, Germany
关键词
bioconjugation; click chemistry; DNA; polymerase chain reaction; solid-phase synthesis;
D O I
10.1002/anie.200802077
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:8350 / 8358
页数:9
相关论文
共 73 条
[1]   Synthesis of oligonucleotides carrying 5′-5′ linkages using copper-catalyzed cycloaddition reactions [J].
Alvira, Margarita ;
Eritja, Ramon .
CHEMISTRY & BIODIVERSITY, 2007, 4 (12) :2798-2809
[2]   Chemoselective formation of successive triazole linkages in one pot: " Click-click" chemistry [J].
Aucagne, Vincent ;
Leigh, David A. .
ORGANIC LETTERS, 2006, 8 (20) :4505-4507
[3]   CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].
Bock, VD ;
Hiemstra, H ;
van Maarseveen, JH .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68
[4]   Microwave assisted "click" chemistry for the synthesis of multiple labeled-carbohydrate oligonucleotides on solid support [J].
Bouillon, Camille ;
Meyer, Albert ;
Vidal, Sebastien ;
Jochum, Anne ;
Chevolot, Yann ;
Cloarec, Jean-Pierre ;
Praly, Jean-Pierre ;
Vasseur, Jean-Jacques ;
Morvan, Francois .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (12) :4700-4702
[5]   Directed DNA metallization [J].
Burley, GA ;
Gierlich, J ;
Mofid, MR ;
Nir, H ;
Tal, S ;
Eichen, Y ;
Carell, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (05) :1398-1399
[6]   Oxidative nucleobase modifications leading to strand scission [J].
Burrows, CJ ;
Muller, JG .
CHEMICAL REVIEWS, 1998, 98 (03) :1109-1151
[7]  
Carell T, 2008, ANGEW CHEM, V120, P3491
[8]   Polytriazoles as copper(I)-stabilizing ligands in catalysis [J].
Chan, TR ;
Hilgraf, R ;
Sharpless, KB ;
Fokin, VV .
ORGANIC LETTERS, 2004, 6 (17) :2853-2855
[9]  
Chevolot Y., 2007, ANGEW CHEM, V119, P2450
[10]   DNA-based carbohydrate biochips: A platform for surface glyco-engineering [J].
Chevolot, Yann ;
Bouillon, Camille ;
Vidal, Sebastien ;
Morvan, Francois ;
Meyer, Albert ;
Cloarec, Jean-Pierre ;
Jochum, Anne ;
Praly, Jean-Pierre ;
Vasseur, Jean-Jacques ;
Souteyrand, Eliane .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2398-2402