Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling

Bring your own copper: Copper-chelating azides undergo much faster click reactions (CuAAC) than nonchelating azides under a variety of biocompatible conditions. This kinetic enhancement allows site-specific protein labeling to be performed on the surface of living cells with only 10–40 μM Cu[supersc...

Full description

Bibliographic Details
Main Authors: Uttamapinant, Chayasith, Tangpeerachaikul, Anupong, Grecian, Scott, Clarke, Scott M., Singh, Upinder, Slade, Peter, Gee, Kyle R., Ting, Alice Y.
Other Authors: Massachusetts Institute of Technology. Department of Chemistry
Format: Article
Language:en_US
Published: Wiley Blackwell 2012
Online Access:http://hdl.handle.net/1721.1/74563
https://orcid.org/0000-0002-8277-5226
_version_ 1826208343477190656
author Uttamapinant, Chayasith
Tangpeerachaikul, Anupong
Grecian, Scott
Clarke, Scott M.
Singh, Upinder
Slade, Peter
Gee, Kyle R.
Ting, Alice Y.
author2 Massachusetts Institute of Technology. Department of Chemistry
author_facet Massachusetts Institute of Technology. Department of Chemistry
Uttamapinant, Chayasith
Tangpeerachaikul, Anupong
Grecian, Scott
Clarke, Scott M.
Singh, Upinder
Slade, Peter
Gee, Kyle R.
Ting, Alice Y.
author_sort Uttamapinant, Chayasith
collection MIT
description Bring your own copper: Copper-chelating azides undergo much faster click reactions (CuAAC) than nonchelating azides under a variety of biocompatible conditions. This kinetic enhancement allows site-specific protein labeling to be performed on the surface of living cells with only 10–40 μM Cu[superscript I]/Cu[superscript II] (see scheme). Detection sensitivity was also increased for CuAAC detection of alkyne-modified proteins and RNA.
first_indexed 2024-09-23T14:04:16Z
format Article
id mit-1721.1/74563
institution Massachusetts Institute of Technology
language en_US
last_indexed 2024-09-23T14:04:16Z
publishDate 2012
publisher Wiley Blackwell
record_format dspace
spelling mit-1721.1/745632022-09-28T18:08:09Z Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling Uttamapinant, Chayasith Tangpeerachaikul, Anupong Grecian, Scott Clarke, Scott M. Singh, Upinder Slade, Peter Gee, Kyle R. Ting, Alice Y. Massachusetts Institute of Technology. Department of Chemistry Ting, Alice Y. Uttamapinant, Chayasith Tangpeerachaikul, Anupong Ting, Alice Y. Bring your own copper: Copper-chelating azides undergo much faster click reactions (CuAAC) than nonchelating azides under a variety of biocompatible conditions. This kinetic enhancement allows site-specific protein labeling to be performed on the surface of living cells with only 10–40 μM Cu[superscript I]/Cu[superscript II] (see scheme). Detection sensitivity was also increased for CuAAC detection of alkyne-modified proteins and RNA. National Institutes of Health (U.S.) (R01 GM072670) 2012-11-05T20:25:58Z 2012-11-05T20:25:58Z 2012-05 2011-11 Article http://purl.org/eprint/type/JournalArticle 1433-7851 1521-3773 http://hdl.handle.net/1721.1/74563 Uttamapinant, Chayasith et al. “Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling.” Angewandte Chemie International Edition 51.24 (2012): 5852–5856. https://orcid.org/0000-0002-8277-5226 en_US http://dx.doi.org/ 10.1002/anie.201108181 Angewandte Chemie International Edition Creative Commons Attribution-Noncommercial-Share Alike 3.0 http://creativecommons.org/licenses/by-nc-sa/3.0/ application/pdf Wiley Blackwell Prof. Ting via Erja Kajosalo
spellingShingle Uttamapinant, Chayasith
Tangpeerachaikul, Anupong
Grecian, Scott
Clarke, Scott M.
Singh, Upinder
Slade, Peter
Gee, Kyle R.
Ting, Alice Y.
Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
title Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
title_full Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
title_fullStr Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
title_full_unstemmed Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
title_short Fast, Cell-Compatible Click Chemistry with Copper-Chelating Azides for Biomolecular Labeling
title_sort fast cell compatible click chemistry with copper chelating azides for biomolecular labeling
url http://hdl.handle.net/1721.1/74563
https://orcid.org/0000-0002-8277-5226
work_keys_str_mv AT uttamapinantchayasith fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling
AT tangpeerachaikulanupong fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling
AT grecianscott fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling
AT clarkescottm fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling
AT singhupinder fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling
AT sladepeter fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling
AT geekyler fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling
AT tingalicey fastcellcompatibleclickchemistrywithcopperchelatingazidesforbiomolecularlabeling