Genetic Encoding and Labeling of Aliphatic Azides and Alkynes in Recombinant Proteins via a Pyrrolysyl-tRNA Synthetase/tRNACUA Pair and Click Chemistry Export

@article{citeulike:4808600, abstract = {We demonstrate that an orthogonal Methanosarcina barkeri MS pyrrolysyl-tRNA synthetase/tRNACUA pair directs the efficient, site-specific incorporation of N6-[(2-propynyloxy)carbonyl]-l-lysine, containing a carbon−carbon triple bond, and N6-[(2-azidoethoxy)carbonyl]-l-lysine, containing an azido group, into recombinant proteins in Escherichia coli. Proteins containing the alkyne functional group are labeled with an azido biotin and an azido fluorophore, via copper catalyzed [3+2] cycloaddtion reactions, to produce the corresponding triazoles in good yield. The methods reported are useful for the site-specific labeling of recombinant proteins and may be combined with mutually orthogonal methods of introducing unnatural amino acids into proteins as well as with chemically orthogonal methods of protein labeling. This should allow the site specific incorporation of multiple distinct probes into proteins and the control of protein topology and structure by intramolecular orthogonal conjugation reactions.}, author = {Nguyen, Duy P. and Lusic, Hrvoje and Neumann, Heinz and Kapadnis, Prashant B. and Deiters, Alexander and Chin, Jason W.}, citeulike-article-id = {4808600}, citeulike-linkout-0 = {http://dx.doi.org/10.1021/ja900553w}, citeulike-linkout-1 = {http://pubs.acs.org/doi/abs/10.1021/ja900553w}, doi = {10.1021/ja900553w}, journal = {Journal of the American Chemical Society}, keywords = {bioconjugation, click-chemistry}, month = {July}, number = {25}, pages = {8720--8721}, posted-at = {2009-06-11 07:38:51}, priority = {2}, title = {Genetic Encoding and Labeling of Aliphatic Azides and Alkynes in Recombinant Proteins via a Pyrrolysyl-tRNA Synthetase/tRNACUA Pair and Click Chemistry}, url = {http://dx.doi.org/10.1021/ja900553w}, volume = {131}, year = {2009} }

TY - JOUR ID - citeulike:4808600 L3 - citeulike-article-id:4808600 N2 - We demonstrate that an orthogonal Methanosarcina barkeri MS pyrrolysyl-tRNA synthetase/tRNACUA pair directs the efficient, site-specific incorporation of N6-[(2-propynyloxy)carbonyl]-l-lysine, containing a carbon−carbon triple bond, and N6-[(2-azidoethoxy)carbonyl]-l-lysine, containing an azido group, into recombinant proteins in Escherichia coli. Proteins containing the alkyne functional group are labeled with an azido biotin and an azido fluorophore, via copper catalyzed [3+2] cycloaddtion reactions, to produce the corresponding triazoles in good yield. The methods reported are useful for the site-specific labeling of recombinant proteins and may be combined with mutually orthogonal methods of introducing unnatural amino acids into proteins as well as with chemically orthogonal methods of protein labeling. This should allow the site specific incorporation of multiple distinct probes into proteins and the control of protein topology and structure by intramolecular orthogonal conjugation reactions. IS - 25 JF - Journal of the American Chemical Society EP - 8721 TI - Genetic Encoding and Labeling of Aliphatic Azides and Alkynes in Recombinant Proteins via a Pyrrolysyl-tRNA Synthetase/tRNACUA Pair and Click Chemistry VL - 131 SP - 8720 KW - bioconjugation KW - click-chemistry AU - Nguyen, Duy AU - Lusic, Hrvoje AU - Neumann, Heinz AU - Kapadnis, Prashant AU - Deiters, Alexander AU - Chin, Jason PY - 2009/07/01/ UR - http://dx.doi.org/10.1021/ja900553w ER -