Stereochemical Basis for Engineered Pyrrolysyl-tRNA Synthetase and the Efficient in Vivo Incorporation of Structurally Divergent Non-native Amino Acids

Takimoto, Jeffrey K.; Dellas, Nikki; Noel, Joseph P.; Wang, Lei

doi:10.1021/cb200057a

Title: Stereochemical Basis for Engineered Pyrrolysyl-tRNA Synthetase and the Efficient in Vivo Incorporation of Structurally Divergent Non-native Amino Acids

Journal Article · Thu May 05 00:00:00 EDT 2011 · ACS Chemical Biology

DOI:https://doi.org/10.1021/cb200057a· OSTI ID:1123355

Takimoto, Jeffrey K. ^[1]; Dellas, Nikki ^[1]; Noel, Joseph P. ^[2]; Wang, Lei ^[1]

The Jack H. Skirball Center for Chemical Biology & Proteomics
The Jack H. Skirball Center for Chemical Biology & Proteomics, Howard Hughes Medical Institute, The Salk Institute for Biological Studies, 10010 North Torrey Pines Road, La Jolla, California 92037, United States

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Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Science (SC), Biological and Environmental Research (BER)

OSTI ID:: 1123355

Journal Information:: ACS Chemical Biology, Journal Name: ACS Chemical Biology Vol. 6 Journal Issue: 7; ISSN 1554-8929

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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References (37)

Pyrrolysine is not hardwired for cotranslational insertion at UAG codons Ambrogelly, A.; Gundllapalli, S.; Herring, S. Proceedings of the National Academy of Sciences, Vol. 104, Issue 9, p. 3141-3146 https://doi.org/10.1073/pnas.0611634104	journal	February 2007
Direct charging of tRNA_CUA with pyrrolysine in vitro and in vivo Blight, Sherry K.; Larue, Ross C.; Mahapatra, Anirban Nature, Vol. 431, Issue 7006, p. 333-335 https://doi.org/10.1038/nature02895	journal	August 2004
Structural basis of nonnatural amino acid recognition by an engineered aminoacyl-tRNA synthetase for genetic code expansion Kobayashi, T.; Sakamoto, K.; Takimura, T. Proceedings of the National Academy of Sciences, Vol. 102, Issue 5 https://doi.org/10.1073/pnas.0407039102	journal	January 2005
Genetic incorporation of unnatural amino acids into proteins in mammalian cells Liu, Wenshe; Brock, Ansgar; Chen, Shuo Nature Methods, Vol. 4, Issue 3 https://doi.org/10.1038/nmeth1016	journal	February 2007
Addition of the keto functional group to the genetic code of Escherichia coli Wang, L.; Zhang, Z.; Brock, A. Proceedings of the National Academy of Sciences, Vol. 100, Issue 1, p. 56-61 https://doi.org/10.1073/pnas.0234824100	journal	December 2002
Pyrrolysine analogues as substrates for pyrrolysyl-tRNA synthetase Polycarpo, Carla R.; Herring, Stephanie; Bérubé, Amélie FEBS Letters, Vol. 580, Issue 28-29 https://doi.org/10.1016/j.febslet.2006.11.028	journal	November 2006
Adding l-lysine derivatives to the genetic code of mammalian cells with engineered pyrrolysyl-tRNA synthetases Mukai, Takahito; Kobayashi, Takatsugu; Hino, Nobumasa Biochemical and Biophysical Research Communications, Vol. 371, Issue 4 https://doi.org/10.1016/j.bbrc.2008.04.164	journal	July 2008
Structural plasticity of an aminoacyl-tRNA synthetase active site Turner, J. M.; Graziano, J.; Spraggon, G. Proceedings of the National Academy of Sciences, Vol. 103, Issue 17 https://doi.org/10.1073/pnas.0601756103	journal	April 2006
Specificity of Pyrrolysyl-tRNA Synthetase for Pyrrolysine and Pyrrolysine Analogs Li, Wen-Tai; Mahapatra, Anirban; Longstaff, David G. Journal of Molecular Biology, Vol. 385, Issue 4 https://doi.org/10.1016/j.jmb.2008.11.032	journal	January 2009
Expanding the Genetic Code of Escherichia coli Wang, L.; Brock, A.; Herberich, B. Science, Vol. 292, Issue 5516, p. 498-500 https://doi.org/10.1126/science.1060077	journal	April 2001
Pyrrolysine Encoded by UAG in Archaea: Charging of a UAG-Decoding Specialized tRNA Srinivasan, G. Science, Vol. 296, Issue 5572 https://doi.org/10.1126/science.1069588	journal	May 2002
A genetically encoded photocaged Nε-methyl-l-lysine Wang, Yane-Shih; Wu, Bo; Wang, Zhiyong Molecular BioSystems, Vol. 6, Issue 9 https://doi.org/10.1039/c002155e	journal	January 2010
The de novo engineering of pyrrolysyl-tRNA synthetase for genetic incorporation of l-phenylalanine and its derivatives Wang, Yane-Shih; Russell, William K.; Wang, Zhiyong Molecular BioSystems, Vol. 7, Issue 3 https://doi.org/10.1039/c0mb00217h	journal	January 2011
The Orbitrap: a new mass spectrometer Hu, Qizhi; Noll, Robert J.; Li, Hongyan Journal of Mass Spectrometry, Vol. 40, Issue 4 https://doi.org/10.1002/jms.856	journal	January 2005
An Enhanced System for Unnatural Amino Acid Mutagenesis in E. coli Young, Travis S.; Ahmad, Insha; Yin, Jun A. Journal of Molecular Biology, Vol. 395, Issue 2 https://doi.org/10.1016/j.jmb.2009.10.030	journal	January 2010
Crystallography & NMR System: A New Software Suite for Macromolecular Structure Determination Brünger, A. T.; Adams, P. D.; Clore, G. M. Acta Crystallographica Section D Biological Crystallography, Vol. 54, Issue 5 https://doi.org/10.1107/S0907444998003254	journal	September 1998
Aminoacyl-tRNA Synthesis Ibba, Michael; Söll, Dieter Annual Review of Biochemistry, Vol. 69, Issue 1 https://doi.org/10.1146/annurev.biochem.69.1.617	journal	June 2000
Pyrrolysyl-tRNA synthetase–tRNA^Pyl structure reveals the molecular basis of orthogonality Nozawa, Kayo; O’Donoghue, Patrick; Gundllapalli, Sarath Nature, Vol. 457, Issue 7233, p. 1163-1167 https://doi.org/10.1038/nature07611	journal	December 2008
PROCHECK: a program to check the stereochemical quality of protein structures Laskowski, R. A.; MacArthur, M. W.; Moss, D. S. Journal of Applied Crystallography, Vol. 26, Issue 2 https://doi.org/10.1107/S0021889892009944	journal	April 1993
New Methods Enabling Efficient Incorporation of Unnatural Amino Acids in Yeast Wang, Qian; Wang, Lei Journal of the American Chemical Society, Vol. 130, Issue 19, p. 6066-6067 https://doi.org/10.1021/ja800894n	journal	May 2008
Multistep Engineering of Pyrrolysyl-tRNA Synthetase to Genetically Encode Nɛ-(o-Azidobenzyloxycarbonyl) lysine for Site-Specific Protein Modification Yanagisawa, Tatsuo; Ishii, Ryohei; Fukunaga, Ryuya Chemistry & Biology, Vol. 15, Issue 11 https://doi.org/10.1016/j.chembiol.2008.10.004	journal	November 2008
A general approach for the generation of orthogonal tRNAs Wang, Lei; Schultz, Peter G. Chemistry & Biology, Vol. 8, Issue 9, p. 883-890 https://doi.org/10.1016/S1074-5521(01)00063-1	journal	September 2001
Crystallographic Studies on Multiple Conformational States of Active-site Loops in Pyrrolysyl-tRNA Synthetase Yanagisawa, Tatsuo; Ishii, Ryohei; Fukunaga, Ryuya Journal of Molecular Biology, Vol. 378, Issue 3 https://doi.org/10.1016/j.jmb.2008.02.045	journal	May 2008
Adding New Chemistries to the Genetic Code Liu, Chang C.; Schultz, Peter G. Annual Review of Biochemistry, Vol. 79, Issue 1, p. 413-444 https://doi.org/10.1146/annurev.biochem.052308.105824	journal	June 2010
Genetically encoding unnatural amino acids for cellular and neuronal studies Wang, Wenyuan; Takimoto, Jeffrey K.; Louie, Gordon V. Nature Neuroscience, Vol. 10, Issue 8 https://doi.org/10.1038/nn1932	journal	July 2007
An Expanded Eukaryotic Genetic Code Chin, Jason W.; Cropp, T. Ashton; Anderson, J. Christopher Science, Vol. 301, Issue 5635, p. 964-967 https://doi.org/10.1126/science.1084772	journal	August 2003
Improving orthogonal tRNA-synthetase recognition for efficient unnatural amino acid incorporation and application in mammalian cells Takimoto, Jeffrey K.; Adams, Katrina L.; Xiang, Zheng Molecular BioSystems, Vol. 5, Issue 9 https://doi.org/10.1039/b904228h	journal	January 2009
Expanding the Genetic Code Wang, Lei; Schultz, Peter G. Angewandte Chemie International Edition, Vol. 44, Issue 1, p. 34-66 https://doi.org/10.1002/anie.200460627	journal	January 2005
The CCP4 suite programs for protein crystallography Acta Crystallographica Section D Biological Crystallography, Vol. 50, Issue 5, p. 760-763 https://doi.org/10.1107/S0907444994003112	journal	September 1994
Expanding the Genetic Code for Biological Studies Wang, Qian; Parrish, Angela R.; Wang, Lei Chemistry & Biology, Vol. 16, Issue 3 https://doi.org/10.1016/j.chembiol.2009.03.001	journal	March 2009
Structure and activity of an aminoacyl-tRNA synthetase that charges tRNA with nitro-tryptophan Buddha, Madhavan R.; Crane, Brian R. Nature Structural & Molecular Biology, Vol. 12, Issue 3 https://doi.org/10.1038/nsmb907	journal	February 2005
Structure of pyrrolysyl-tRNA synthetase, an archaeal enzyme for genetic code innovation Kavran, J. M.; Gundllapalli, S.; O'Donoghue, P. Proceedings of the National Academy of Sciences, Vol. 104, Issue 27 https://doi.org/10.1073/pnas.0704769104	journal	June 2007
A genetically encoded fluorescent amino acid Summerer, D.; Chen, S.; Wu, N. Proceedings of the National Academy of Sciences, Vol. 103, Issue 26, p. 9785-9789 https://doi.org/10.1073/pnas.0603965103	journal	June 2006
Adding pyrrolysine to the Escherichia coli genetic code Namy, Olivier; Zhou, Yu; Gundllapalli, Sarath FEBS Letters, Vol. 581, Issue 27 https://doi.org/10.1016/j.febslet.2007.10.022	journal	October 2007
A Facile System for Encoding Unnatural Amino Acids in Mammalian Cells Chen, Peng R.; Groff, Dan; Guo, Jiantao Angewandte Chemie International Edition, Vol. 48, Issue 22 https://doi.org/10.1002/anie.200900683	journal	May 2009
Synthesis of Glu-tRNA ^Gln by Engineered and Natural Aminoacyl-tRNA Synthetases Rodríguez-Hernández, Annia; Bhaskaran, Hari; Hadd, Andrew Biochemistry, Vol. 49, Issue 31 https://doi.org/10.1021/bi100886z	journal	August 2010
Indirect Readout of tRNA for Aminoacylation Perona, John J.; Hou, Ya-Ming Biochemistry, Vol. 46, Issue 37 https://doi.org/10.1021/bi7014647	journal	August 2007

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