Clicking 1,2,4,5-tetrazine and cyclooctynes with tunable reaction rates

被引：159

作者：

Chen, Weixuan

Wang, Danzhu

Dai, Chaofeng

Hamelberg, Donald

Wang, Binghe ^{[1
]}

机构：

[1] Georgia State Univ, Dept Chem, Ctr Biotechnol & Drug Design, Atlanta, GA 30302 USA

来源：

CHEMICAL COMMUNICATIONS | 2012年 / 48卷 / 12期

基金：

美国国家卫生研究院;

关键词：

COPPER-FREE; CHEMISTRY; LIGATION; SELECTIVITY; DESIGN; CELLS;

D O I：

10.1039/c2cc16716f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Substituted tetrazines have been found to undergo facile inverse electron demand Diels-Alder reactions with "tunable'' reaction rates.

引用

页码：1736 / 1738

页数：3

共 31 条

[1] THE REACTIVITY OF NITROGEN HETEROCYCLICS WITH RESPECT TO CYCLOOCTYNE AS THE DIENOPHILE [J].

BALCAR, J ;

CHRISAM, G ;

HUBER, FX ;

SAUER, J .

TETRAHEDRON LETTERS, 1983, 24 (14) :1481-1484

[2] Click Chemistry and Bioorthogonal Reactions: Unprecedented Selectivity in the Labeling of Biological Molecules [J].

Best, Michael D. .

BIOCHEMISTRY, 2009, 48 (28) :6571-6584

[3] Tetrazine ligation: Fast bioconjugation based on inverse-electron-demand Diels-Alder reactivity [J].

Blackman, Melissa L. ;

Royzen, Maksim ;

Fox, Joseph M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13518-+

[4] Second-generation difluorinated cyclooctynes for copper-free click chemistry [J].

Codelli, Julian A. ;

Baskin, Jeremy M. ;

Agard, Nicholas J. ;

Berozzi, Carolyn R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (34) :11486-11493

[5] The first chemical synthesis of boronic acid-modified DNA through a copper-free click reaction [J].

Dai, Chaofeng ;

Wang, Lifang ;

Sheng, Jia ;

Peng, Hanjing ;

Draganov, Alexander Boryanov ;

Huang, Zhen ;

Wang, Binghe .

CHEMICAL COMMUNICATIONS, 2011, 47 (12) :3598-3600

[6] Aza-dibenzocyclooctynes for fast and efficient enzyme PEGylation via copper-free (3+2) cycloaddition [J].

Debets, Marjoke F. ;

van Berkel, Sander S. ;

Schoffelen, Sanne ;

Rutjes, Floris P. J. T. ;

van Hest, Jan C. M. ;

van Delft, Floris L. .

CHEMICAL COMMUNICATIONS, 2010, 46 (01) :97-99

[7] Fast and Sensitive Pretargeted Labeling of Cancer Cells through a Tetrazine/trans-Cyclooctene Cycloaddition [J].

Devaraj, Neal K. ;

Upadhyay, Rabi ;

Hatin, Jered B. ;

Hilderbrand, Scott A. ;

Weissleder, Ralph .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :7013-7016

[8] Readily Accessible Bicyclononynes for Bioorthogonal Labeling and Three-Dimensional Imaging of Living Cells [J].

Dommerholt, Jan ;

Schmidt, Samuel ;

Temming, Rinske ;

Hendriks, Linda J. A. ;

Rutjes, Floris P. J. T. ;

van Hest, Jan C. M. ;

Lefeber, Dirk J. ;

Friedl, Peter ;

van Delft, Floris L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9422-9425

[9] Rapid Cu-Free Click Chemistry with Readily Synthesized Biarylazacyclooctynones [J].

Jewett, John C. ;

Sletten, Ellen M. ;

Bertozzi, Carolyn R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3688-+

[10] The Staudinger ligation -: A gift to chemical biology' [J].

Köhn, M ;

Breinbauer, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (24) :3106-3116

← 1 2 3 4 →