Two Rapid Catalyst-Free Click Reactions for In Vivo Protein Labeling of Genetically Encoded Strained Alkene/Alkyne Functionalities | Zendy

Yadagiri Kurra | Zendy; Keturah A. Odoi | Zendy; YanJiun Lee | Zendy; Yanyan Yang | Zendy; Tongxiang Lu | Zendy; Steven E. Wheeler | Zendy; Jessica TorresKolbus | Zendy; Alexander Deiters | Zendy; Wenshe Ray Liu | Zendy

Open Access

Two Rapid Catalyst-Free Click Reactions for In Vivo Protein Labeling of Genetically Encoded Strained Alkene/Alkyne Functionalities

Author(s) -

Yadagiri Kurra,

Keturah A. Odoi,

YanJiun Lee,

Yanyan Yang,

Tongxiang Lu,

Steven E. Wheeler,

Jessica TorresKolbus,

Alexander Deiters,

Wenshe Ray Liu

Publication year - 2014

Publication title -

bioconjugate chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.279

H-Index - 172

eISSN - 1520-4812

pISSN - 1043-1802

DOI - 10.1021/bc500361d

Subject(s) - chemistry , alkyne , alkene , norbornene , click chemistry , cycloaddition , cyclooctene , tetrazine , bioorthogonal chemistry , bioconjugation , combinatorial chemistry , catalysis , organic chemistry , polymerization , polymer

Detailed kinetic analyses of inverse electron-demand Diels–Alder cycloaddition and nitrilimine-alkene/alkyne 1,3-diploar cycloaddition reactions were conducted and the reactions were applied for rapid protein bioconjugation. When reacted with a tetrazine or a diaryl nitrilimine, strained alkene/alkyne entities including norbornene, trans-cyclooctene, and cyclooctyne displayed rapid kinetics. To apply these “click” reactions for site-specific protein labeling, five tyrosine derivatives that contain a norbornene, trans-cyclooctene, or cyclooctyne entity were genetically encoded into proteins in Escherichia coli using an engineered pyrrolysyl-tRNA synthetase-tRNA(CUA)(Pyl) pair. Proteins bearing these noncanonical amino acids were successively labeled with a fluorescein tetrazine dye and a diaryl nitrilimine both in vitro and in living cells.

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