A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface

[Image: see text] The merging of site-specific incorporation of small bioorthogonal functional groups into proteins via amber codon suppression with bioorthogonal chemistry has created exciting opportunities to extend the power of organic reactions to living systems. Here we show that a new alkyne a...

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Autores principales: Li, Nan, Ramil, Carlo P., Lim, Reyna K. V., Lin, Qing
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4340352/
https://www.ncbi.nlm.nih.gov/pubmed/25347611
http://dx.doi.org/10.1021/cb500649q
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author Li, Nan
Ramil, Carlo P.
Lim, Reyna K. V.
Lin, Qing
author_facet Li, Nan
Ramil, Carlo P.
Lim, Reyna K. V.
Lin, Qing
author_sort Li, Nan
collection PubMed
description [Image: see text] The merging of site-specific incorporation of small bioorthogonal functional groups into proteins via amber codon suppression with bioorthogonal chemistry has created exciting opportunities to extend the power of organic reactions to living systems. Here we show that a new alkyne amino acid can be site-selectively incorporated into mammalian proteins via a known orthogonal pyrrolysyl-tRNA synthetase/tRNA(CUA) pair and directs an unprecedented, palladium-mediated cross-coupling reaction-driven protein labeling on live mammalian cell surface. A comparison study with the alkyne-encoded proteins in vitro indicated that this terminal alkyne is better suited for the palladium-mediated cross-coupling reaction than the copper-catalyzed click chemistry.
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spelling pubmed-43403522015-10-27 A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface Li, Nan Ramil, Carlo P. Lim, Reyna K. V. Lin, Qing ACS Chem Biol [Image: see text] The merging of site-specific incorporation of small bioorthogonal functional groups into proteins via amber codon suppression with bioorthogonal chemistry has created exciting opportunities to extend the power of organic reactions to living systems. Here we show that a new alkyne amino acid can be site-selectively incorporated into mammalian proteins via a known orthogonal pyrrolysyl-tRNA synthetase/tRNA(CUA) pair and directs an unprecedented, palladium-mediated cross-coupling reaction-driven protein labeling on live mammalian cell surface. A comparison study with the alkyne-encoded proteins in vitro indicated that this terminal alkyne is better suited for the palladium-mediated cross-coupling reaction than the copper-catalyzed click chemistry. American Chemical Society 2014-10-27 2015-02-20 /pmc/articles/PMC4340352/ /pubmed/25347611 http://dx.doi.org/10.1021/cb500649q Text en Copyright © 2014 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Li, Nan
Ramil, Carlo P.
Lim, Reyna K. V.
Lin, Qing
A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface
title A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface
title_full A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface
title_fullStr A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface
title_full_unstemmed A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface
title_short A Genetically Encoded Alkyne Directs Palladium-Mediated Protein Labeling on Live Mammalian Cell Surface
title_sort genetically encoded alkyne directs palladium-mediated protein labeling on live mammalian cell surface
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4340352/
https://www.ncbi.nlm.nih.gov/pubmed/25347611
http://dx.doi.org/10.1021/cb500649q
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