Cu-free click cycloaddition reactions in chemical biology

被引:1344
作者
Jewett, John C. [1 ]
Bertozzi, Carolyn R. [1 ,2 ,3 ,4 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Dept Mol & Cell Biol, Berkeley, CA 94720 USA
[3] Univ Calif Berkeley, Howard Hughes Med Inst, Berkeley, CA 94720 USA
[4] Lawrence Berkeley Natl Lab, Berkeley, CA 94720 USA
关键词
AZIDE-ALKYNE CYCLOADDITION; FREE TRIAZOLE FORMATION; COPPER-FREE; 1,3-DIPOLAR CYCLOADDITIONS; TERMINAL ALKYNES; LIVING CELLS; CANCER-CELLS; CHEMISTRY; LIGATION; BIOCONJUGATION;
D O I
10.1039/b901970g
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
Bioorthogonal chemical reactions are paving the way for new innovations in biology. These reactions possess extreme selectivity and biocompatibility, such that their participating reagents can form covalent bonds within richly functionalized biological systems-in some cases, living organisms. This tutorial review will summarize the history of this emerging field, as well as recent progress in the development and application of bioorthogonal copper-free click cycloaddition reactions.
引用
收藏
页码:1272 / 1279
页数:8
相关论文
共 47 条
[1]
A comparative study of bioorthogonal reactions with azides [J].
Agard, Nicholas J. ;
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Lo, Anderson ;
Bertozzi, Carolyn R. .
ACS CHEMICAL BIOLOGY, 2006, 1 (10) :644-648
[2]
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
[3]
[Anonymous], 1984, 13 DIPOLAR CYCLOADDI
[4]
Anslyn E.V., 2006, MODERN PHYS ORGANIC, P111
[5]
Ring Strain Energy in the Cyclooctyl System. The Effect of Strain Energy on [3+2] Cycloaddition Reactions with Azides [J].
Bach, Robert D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (14) :5233-5243
[6]
Copper-free click chemistry for dynamic in vivo imaging [J].
Baskin, Jeremy M. ;
Prescher, Jennifer A. ;
Laughlin, Scott T. ;
Agard, Nicholas J. ;
Chang, Pamela V. ;
Miller, Isaac A. ;
Lo, Anderson ;
Codelli, Julian A. ;
Bertozzi, Carolyn R. .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2007, 104 (43) :16793-16797
[7]
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-+
[8]
BUHL H, 1978, SYNTHESIS-STUTTGART, P536
[9]
Chambers R., 2004, Fluorine in Organic Chemistry, P14
[10]
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