Advances in 1,3-dipolar cycloaddition reaction of azides and alkynes - A prototype of "click" chemistry

被引:111
作者
Wang, Q [1 ]
Chittaboina, S [1 ]
Barnhill, HN [1 ]
机构
[1] Univ S Carolina, Dept Chem & Biochem, Columbia, SC 29208 USA
关键词
D O I
10.2174/1570178054038885
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Click chemistry, designated by Sharpless and his coworkers, is a modular approach that uses only the most practical and reliable chemical transformations. The Huisgen reaction, especially the newly developed copper(l)-catalyzed 1,2,3-triazole formation reaction between azides and alkynes, is regarded as the "cream of the crop" of click chemistry. In this review, we introduce the recent development of this reaction, and highlight some of its important applications in drug discovery, bioconjugation chemistry, materials development and surface modification.
引用
收藏
页码:293 / 301
页数:9
相关论文
共 79 条
[1]   A strain-promoted [3+2] azide-alkyne cycloaddition for covalent modification of blomolecules in living systems [J].
Agard, NJ ;
Prescher, JA ;
Bertozzi, CR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (46) :15046-15047
[2]   A versatile synthesis of fused triazolo derivatives by sequential Ugi/alkyne-azide cycloaddition reactions [J].
Akritopoulou-Zanze, I ;
Gracias, V ;
Djuric, SW .
TETRAHEDRON LETTERS, 2004, 45 (46) :8439-8441
[3]   Combining ring-opening metathesis polymerization (ROMP) with sharpless-type "click" reactions: An easy method for the preparation of side chain functionalized poly(oxynorbornenes) [J].
Binder, WH ;
Kluger, C .
MACROMOLECULES, 2004, 37 (25) :9321-9330
[4]   Synthesis of readily modifiable cyclodextrin analogues via cyclodimerization of an alkynyl-azido trisaccharide [J].
Bodine, KD ;
Gin, DY ;
Gin, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1638-1639
[5]   Freeze-frame inhibitor captures acetylcholinesterase in a unique conformation [J].
Bourne, Y ;
Kolb, HC ;
Radic, Z ;
Sharpless, KB ;
Taylor, P ;
Marchot, P .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2004, 101 (06) :1449-1454
[6]   Azide-alkyne coupling:: A powerful reaction for bioconjugate chemistry [J].
Breinbauer, R ;
Köhn, M .
CHEMBIOCHEM, 2003, 4 (11) :1147-1149
[7]   Rapid diversity-oriented synthesis in microtiter plates for in situ screening of HIV protease inhibitors [J].
Brik, A ;
Muldoon, J ;
Lin, YC ;
Elder, JH ;
Goodsell, DS ;
Olson, AJ ;
Fokin, VV ;
Sharpless, KB ;
Wong, CH .
CHEMBIOCHEM, 2003, 4 (11) :1246-1248
[8]   Covalent display of oligosaccharide arrays in microtiter plates [J].
Bryan, MC ;
Fazio, F ;
Lee, HK ;
Huang, CY ;
Chang, A ;
Best, MD ;
Calarese, DA ;
Blixt, C ;
Paulson, JC ;
Burton, D ;
Wilson, IA ;
Wong, CH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8640-8641
[9]   High-throughput identification of fucosyltransferase inhibitors using carbohydrate microarrays [J].
Bryan, MC ;
Lee, LV ;
Wong, CH .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2004, 14 (12) :3185-3188
[10]   Convenient methods for the synthesis of ferrocene-carbohydrate conjugates [J].
Casas-Solvas, JM ;
Vargas-Berenguel, A ;
Capitán-Vallvey, LF ;
Santoyo-González, F .
ORGANIC LETTERS, 2004, 6 (21) :3687-3690