Thiacycloalkynes for Copper-Free Click Chemistry

被引：130

作者：

de Almeida, Gabriela ^{[1
]}

Sletten, Ellen M. ^{[1
]}

Nakamura, Hitomi ^{[1
]}

Palaniappan, Krishnan K. ^{[1
]}

Bertozzi, Carolyn R. ^{[1
,2
,3
]}

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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 10期

关键词：

bioorthogonal chemistry; click chemistry; protein modifications; strained alkynes; sulfur heterocycles; 1,3-DIPOLAR CYCLOADDITIONS; LIVING ANIMALS; REACTIVITY; CELLS; CYCLOOCTYNES; ACETYLENES; GENERATION; LIGATION; PROTEIN; ALKYNES;

D O I：

10.1002/anie.201106325

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The heteroatom helps! The introduction of an endocyclic sulfur atom enables fine-tuning of the reactivity and stability of thiacycloalkynes for copper-free click chemistry. The stabilizing effect of the endocyclic sulfur atom allows the use of highly activated seven-membered rings as reagents for bioorthogonal copper-free click chemistry. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：2443 / 2447

页数：5

共 35 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]

Banert K., 2011, ANGEW CHEM, V123, P6295

[3] Synthesis with Perfect Atom Economy: Generation of Diazo Ketones by 1,3-Dipolar Cycloaddition of Nitrous Oxide at Cyclic Alkynes under Mild Conditions [J].

Banert, Klaus ;

Plefka, Oliver .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (27) :6171-6174

[4] 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-+

[5] Metabolic cross-talk allows labeling of O-linked β-N-acetylglucosamine-modified proteins via the N-acetylgalactosamine salvage pathway [J].

Boyce, Michael ;

Carrico, Isaac S. ;

Ganguli, Anjali S. ;

Yu, Seok-Ho ;

Hangauer, Matthew J. ;

Hubbard, Sarah C. ;

Kohler, Jennifer J. ;

Bertozzi, Carolyn R. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (08) :3141-3146

[6] 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

[7] Cyclooctyne-based reagents for uncatalyzed click chemistry: A computational survey [J].

Chenoweth, Kimberly ;

Chenoweth, David ;

Goddard, William A., III .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (24) :5255-5258

[8] Direct epoxidation of D-glucal and D-galactal derivatives with in situ generated DMDO [J].

Cheshev, Pavel ;

Marra, Alberto ;

Dondoni, Alessandro .

CARBOHYDRATE RESEARCH, 2006, 341 (16) :2714-2716

[9] 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

[10] 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

← 1 2 3 4 →