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

Two Rapid Catalyst-Free Click Reactions for In Vivo Protein Labeling of Genetically Encoded Strained Alkene/Alkyne Functionalities. Kurra, Y., Odoi, K. A., Lee, Y., Yang, Y., Lu, T., Wheeler, S. E., Torres-Kolbus, J., Deiters, A., & Liu, W. R. Bioconjugate Chemistry, 25(9):1730–1738, September, 2014.

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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-tRNACPyUlA 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.

@article{kurra_two_2014,
	title = {Two {Rapid} {Catalyst}-{Free} {Click} {Reactions} for {In} {Vivo} {Protein} {Labeling} of {Genetically} {Encoded} {Strained} {Alkene}/{Alkyne} {Functionalities}},
	volume = {25},
	issn = {1043-1802, 1520-4812},
	url = {https://pubs.acs.org/doi/10.1021/bc500361d},
	doi = {10.1021/bc500361d},
	abstract = {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-tRNACPyUlA 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.},
	language = {en},
	number = {9},
	urldate = {2021-11-24},
	journal = {Bioconjugate Chemistry},
	author = {Kurra, Yadagiri and Odoi, Keturah A. and Lee, Yan-Jiun and Yang, Yanyan and Lu, Tongxiang and Wheeler, Steven E. and Torres-Kolbus, Jessica and Deiters, Alexander and Liu, Wenshe R.},
	month = sep,
	year = {2014},
	pages = {1730--1738},
}

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