Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne

Efficient access to proteins modified site-specifically with glycans is important in glycobiology and for therapeutic applications. Herein, we report a biocompatible protein glycoconjugation by inverse demand Diels–Alder reaction between tetrazine and trans-cyclooctene. Tetrazine functionalized glyc...

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Autores principales: Machida, Takuya, Lang, Kathrin, Xue, Lin, Chin, Jason W., Winssinger, Nicolas
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4673905/
https://www.ncbi.nlm.nih.gov/pubmed/25897481
http://dx.doi.org/10.1021/acs.bioconjchem.5b00101
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author Machida, Takuya
Lang, Kathrin
Xue, Lin
Chin, Jason W.
Winssinger, Nicolas
author_facet Machida, Takuya
Lang, Kathrin
Xue, Lin
Chin, Jason W.
Winssinger, Nicolas
author_sort Machida, Takuya
collection PubMed
description Efficient access to proteins modified site-specifically with glycans is important in glycobiology and for therapeutic applications. Herein, we report a biocompatible protein glycoconjugation by inverse demand Diels–Alder reaction between tetrazine and trans-cyclooctene. Tetrazine functionalized glycans were obtained in one step by CuAAC (Cu-catalyzed alkyne azide cycloaddition) between glycosyl azide and an alkyne-tetrazine adduct. Site-specific glycoconjugation was performed chemoselectively on a target protein in which a trans-cyclooctene derivatized lysine was genetically encoded. Glycoconjugation proceeded to completion on purified protein and was shown to be selective for the target protein in E. coli.
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spelling pubmed-46739052015-12-09 Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne Machida, Takuya Lang, Kathrin Xue, Lin Chin, Jason W. Winssinger, Nicolas Bioconjug Chem Article Efficient access to proteins modified site-specifically with glycans is important in glycobiology and for therapeutic applications. Herein, we report a biocompatible protein glycoconjugation by inverse demand Diels–Alder reaction between tetrazine and trans-cyclooctene. Tetrazine functionalized glycans were obtained in one step by CuAAC (Cu-catalyzed alkyne azide cycloaddition) between glycosyl azide and an alkyne-tetrazine adduct. Site-specific glycoconjugation was performed chemoselectively on a target protein in which a trans-cyclooctene derivatized lysine was genetically encoded. Glycoconjugation proceeded to completion on purified protein and was shown to be selective for the target protein in E. coli. 2015-04-24 2015-05-20 /pmc/articles/PMC4673905/ /pubmed/25897481 http://dx.doi.org/10.1021/acs.bioconjchem.5b00101 Text en This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://creativecommons.org/licenses/by/4.0/) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
spellingShingle Article
Machida, Takuya
Lang, Kathrin
Xue, Lin
Chin, Jason W.
Winssinger, Nicolas
Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne
title Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne
title_full Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne
title_fullStr Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne
title_full_unstemmed Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne
title_short Site-Specific Glycoconjugation of Protein via Bioorthogonal Tetrazine Cycloaddition with a Genetically Encoded trans-Cyclooctene or Bicyclononyne
title_sort site-specific glycoconjugation of protein via bioorthogonal tetrazine cycloaddition with a genetically encoded trans-cyclooctene or bicyclononyne
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4673905/
https://www.ncbi.nlm.nih.gov/pubmed/25897481
http://dx.doi.org/10.1021/acs.bioconjchem.5b00101
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