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Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry
[Image: see text] The 1,3-dipolar cycloaddition of azides and activated alkynes has been used for site-selective labeling of biomolecules in vitro and in vivo. While copper catalysis has been widely employed to activate terminal alkynes for [3 + 2] cycloaddition, this method, often termed “click che...
Autores principales: | , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2008
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2646667/ https://www.ncbi.nlm.nih.gov/pubmed/18680289 http://dx.doi.org/10.1021/ja803086r |
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author | Codelli, Julian A. Baskin, Jeremy M. Agard, Nicholas J. Bertozzi, Carolyn R. |
author_facet | Codelli, Julian A. Baskin, Jeremy M. Agard, Nicholas J. Bertozzi, Carolyn R. |
author_sort | Codelli, Julian A. |
collection | PubMed |
description | [Image: see text] The 1,3-dipolar cycloaddition of azides and activated alkynes has been used for site-selective labeling of biomolecules in vitro and in vivo. While copper catalysis has been widely employed to activate terminal alkynes for [3 + 2] cycloaddition, this method, often termed “click chemistry”, is currently incompatible with living systems because of the toxicity of the metal. We recently reported a difluorinated cyclooctyne (DIFO) reagent that rapidly reacts with azides in living cells without the need for copper catalysis. Here we report a novel class of DIFO reagents for copper-free click chemistry that are considerably more synthetically tractable. The new analogues maintained the same elevated rates of [3 + 2] cycloaddition as the parent compound and were used for imaging glycans on live cells. These second-generation DIFO reagents should expand the use of copper-free click chemistry in the hands of biologists. |
format | Text |
id | pubmed-2646667 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-26466672009-03-20 Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry Codelli, Julian A. Baskin, Jeremy M. Agard, Nicholas J. Bertozzi, Carolyn R. J Am Chem Soc [Image: see text] The 1,3-dipolar cycloaddition of azides and activated alkynes has been used for site-selective labeling of biomolecules in vitro and in vivo. While copper catalysis has been widely employed to activate terminal alkynes for [3 + 2] cycloaddition, this method, often termed “click chemistry”, is currently incompatible with living systems because of the toxicity of the metal. We recently reported a difluorinated cyclooctyne (DIFO) reagent that rapidly reacts with azides in living cells without the need for copper catalysis. Here we report a novel class of DIFO reagents for copper-free click chemistry that are considerably more synthetically tractable. The new analogues maintained the same elevated rates of [3 + 2] cycloaddition as the parent compound and were used for imaging glycans on live cells. These second-generation DIFO reagents should expand the use of copper-free click chemistry in the hands of biologists. American Chemical Society 2008-08-05 2008-08-27 /pmc/articles/PMC2646667/ /pubmed/18680289 http://dx.doi.org/10.1021/ja803086r Text en Copyright © 2008 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org. 40.75 |
spellingShingle | Codelli, Julian A. Baskin, Jeremy M. Agard, Nicholas J. Bertozzi, Carolyn R. Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry |
title | Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry |
title_full | Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry |
title_fullStr | Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry |
title_full_unstemmed | Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry |
title_short | Second-Generation Difluorinated Cyclooctynes for Copper-Free Click Chemistry |
title_sort | second-generation difluorinated cyclooctynes for copper-free click chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2646667/ https://www.ncbi.nlm.nih.gov/pubmed/18680289 http://dx.doi.org/10.1021/ja803086r |
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