Site specific incorporation of keto amino acids into proteins

Schultz, Peter G; Wang, Lei

Title: Site specific incorporation of keto amino acids into proteins

Patent · Tue Dec 06 00:00:00 EST 2011

OSTI ID:1034342

Schultz, Peter G ^[1]; Wang, Lei ^[2]

La Jolla, CA
San Diego, CA

Compositions and methods of producing components of protein biosynthetic machinery that include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, and orthogonal pairs of tRNAs/synthetases, which incorporate keto amino acids into proteins are provided. Methods for identifying these orthogonal pairs are also provided along with methods of producing proteins with keto amino acids using these orthogonal pairs.

View Patent

Cite

Export

Save

Research Organization:: The Scripps Research Inst., La Jolla, CA (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: FG03-00ER45812; AC03-76SF00098

Assignee:: The Scripps Research Institute (La Jolla, CA)

Patent Number(s):: 8,071,344

Application Number:: 11/978,182

OSTI ID:: 1034342

Country of Publication:: United States

Language:: English

References (132)

Twenty-first aminoacyl-tRNA synthetase-suppressor tRNA pairs for possible use in site-specific incorporation of amino acid analogues into proteins in eukaryotes and in eubacteria Kowal, A. K.; Kohrer, C.; RajBhandary, U. L. Proceedings of the National Academy of Sciences, Vol. 98, Issue 5, p. 2268-2273 https://doi.org/10.1073/pnas.031488298	journal	January 2001
Engineering Chemical Reactivity on Cell Surfaces Through Oligosaccharide Biosynthesis Mahal, Lara K.; Yarema, Kevin J.; Bertozzi, Carolyn R. Science, Vol. 276, Issue 5315, p. 1125-1128 https://doi.org/10.1126/science.276.5315.1125	journal	May 1997
Bio–incorporation of telluromethionine into buried residues of dihydrofolate reductase Boles, Jeffrey O.; Lewinski, Krzysztof; Kunkle, Marci Nature Structural & Molecular Biology, Vol. 1, Issue 5, p. 283-284 https://doi.org/10.1038/nsb0594-283	journal	May 1994
An unnatural base pair for incorporating amino acid analogs into proteins Hirao, Ichiro; Ohtsuki, Takashi; Fujiwara, Tsuyoshi Nature Biotechnology, Vol. 20, Issue 2 https://doi.org/10.1038/nbt0202-177	journal	February 2002
Site-specific incorporation of novel backbone structures into proteins Ellman, J.; Mendel, D.; Schultz, P. Science, Vol. 255, Issue 5041 https://doi.org/10.1126/science.1553546	journal	January 1992
An engineered Escherichia coli tyrosyl-tRNA synthetase for site-specific incorporation of an unnatural amino acid into proteins in eukaryotic translation and its application in a wheat germ cell-free system Kiga, D.; Sakamoto, K.; Kodama, K. Proceedings of the National Academy of Sciences, Vol. 99, Issue 15, p. 9715-9720 https://doi.org/10.1073/pnas.142220099	journal	July 2002
In vitro protein engineering using synthetic tRNAAla with different anticodons Ma, Chunhua; Kudlicki, Wieslaw; Odom, O. W. Biochemistry, Vol. 32, Issue 31 https://doi.org/10.1021/bi00082a015	journal	August 1993
Direct Physical Measure of Conformational Rearrangement Underlying Potassium Channel Gating Mannuzzu, L. M.; Moronne, M. M.; Isacoff, E. Y. Science, Vol. 271, Issue 5246 https://doi.org/10.1126/science.271.5246.213	journal	January 1996
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
Addition of p-Azido-L-phenylalanine to the Genetic Code of Escherichia coli Chin, Jason W.; Santoro, Stephen W.; Martin, Andrew B. Journal of the American Chemical Society, Vol. 124, Issue 31, p. 9026-9027 https://doi.org/10.1021/ja027007w	journal	July 2002
An efficient system for the evolution of aminoacyl-tRNA synthetase specificity Santoro, Stephen W.; Wang, Lei; Herberich, Brad Nature Biotechnology, Vol. 20, Issue 10 https://doi.org/10.1038/nbt742	journal	September 2002
Modification of the amino acid specificity of tyrosyl-tRNA synthetase by protein engineering de Prat Gay, Gonzalo; Duckworth, Harry W.; Fersht, Alan R. FEBS Letters, Vol. 318, Issue 2, p. 167-171 https://doi.org/10.1016/0014-5793(93)80014-L	journal	March 1993
Flash Decaging of Tyrosine Sidechains in an Ion Channel Miller, Jeffrey C.; Silverman, Scott K.; England, Pamela M. Neuron, Vol. 20, Issue 4, p. 619-624 https://doi.org/10.1016/S0896-6273(00)81001-6	journal	April 1998
Synthesis of 4-substituted prolines as conformationally constrained amino acid analogs Koskinen, Ari M. P.; Rapoport, Henry The Journal of Organic Chemistry, Vol. 54, Issue 8 https://doi.org/10.1021/jo00269a022	journal	April 1989
Probing the Structure and Function of the Tachykinin Neurokinin-2 Receptor through Biosynthetic Incorporation of Fluorescent Amino Acids at Specific Sites Turcatti, Gerardo; Nemeth, Karin; Edgerton, Michael D. Journal of Biological Chemistry, Vol. 271, Issue 33 https://doi.org/10.1074/jbc.271.33.19991	journal	August 1996
Selenocysteine: the 21st amino acid Böck, A.; Forchhammer, K.; Heider, J. Molecular Microbiology, Vol. 5, Issue 3 https://doi.org/10.1111/j.1365-2958.1991.tb00722.x	journal	March 1991
Relaxing the substrate specificity of an aminoacyl-tRNA synthetase allows in vitro and in vivo synthesis of proteins containing unnatural amino acids Ibba, Michael; Hennecke, Hauke FEBS Letters, Vol. 364, Issue 3, p. 272-275 https://doi.org/10.1016/0014-5793(95)00408-2	journal	May 1995
A set of plasmids constitutively producing different RNA levels in Escherichia coli Gabriel, Kay; McClain, William H. Journal of Molecular Biology, Vol. 290, Issue 2 https://doi.org/10.1006/jmbi.1999.2885	journal	July 1999
Efforts toward Expansion of the Genetic Alphabet: Replication of DNA with Three Base Pairs Tae, Eunju Lee; Wu, Yiqin; Xia, Gang Journal of the American Chemical Society, Vol. 123, Issue 30 https://doi.org/10.1021/ja010731e	journal	August 2001
Photocrosslinking of the signal sequence of nascent preprolactin to the 54-kilodalton polypeptide of the signal recognition particle. Krieg, U. C.; Walter, P.; Johnson, A. E. Proceedings of the National Academy of Sciences, Vol. 83, Issue 22 https://doi.org/10.1073/pnas.83.22.8604	journal	November 1986
Adding l-3-(2-Naphthyl)alanine to the Genetic Code of E. coli Wang, Lei; Brock, Ansgar; Schultz, Peter G. Journal of the American Chemical Society, Vol. 124, Issue 9, p. 1836-1837 https://doi.org/10.1021/ja012307j	journal	March 2002
Selenomethionyl proteins produced for analysis by multiwavelength anomalous diffraction (MAD): a vehicle for direct determination of three-dimensional structure. Hendrickson, W. A.; Horton, J. R.; LeMaster, D. M. The EMBO Journal, Vol. 9, Issue 5 https://doi.org/10.1002/j.1460-2075.1990.tb08287.x	journal	May 1990
Evolutionary relationship between Halobacterium cutirubrum and eukaryotes determined by use of aminoacyl-tRNA synthetases as phylogenetic probes Kwok, Yau; Wong, J. Tze-Fei Canadian Journal of Biochemistry, Vol. 58, Issue 3 https://doi.org/10.1139/o80-029	journal	March 1980
[15] Biosynthetic method for introducing unnatural amino acids site-specifically into proteins Ellman, Jon; Mendel, David; Anthony-Cahill, Spencer Molecular Design and Modeling: Concepts and Applications Part A: Proteins, Peptides, and Enzymes, p. 301-336 https://doi.org/10.1016/0076-6879(91)02017-4	book	January 1991
Human Tyrosyl-tRNA Synthetase Shares Amino Acid Sequence Homology with a Putative Cytokine Kleeman, Theresa A.; Wei, Dongbing; Simpson, Keith L. Journal of Biological Chemistry, Vol. 272, Issue 22 https://doi.org/10.1074/jbc.272.22.14420	journal	May 1997
Expanding tRNA recognition of a tRNA synthetase by a single amino acid change Feng, L.; Tumbula-Hansen, D.; Toogood, H. Proceedings of the National Academy of Sciences, Vol. 100, Issue 10, p. 5676-5681 https://doi.org/10.1073/pnas.0631525100	journal	May 2003
Rational Design of an Unnatural Base Pair with Increased Kinetic Selectivity Ogawa, Anthony K.; Wu, Yiqin; Berger, Markus Journal of the American Chemical Society, Vol. 122, Issue 36, p. 8803-8804 https://doi.org/10.1021/ja001450u	journal	September 2000
Unnatural amino acids as probes of protein structure and function Dougherty, D. Current Opinion in Chemical Biology, Vol. 4, Issue 6, p. 645-652 https://doi.org/10.1016/S1367-5931(00)00148-4	journal	December 2000
TRNA2Gln Su+2 mutants that increase amber suppression. Bradley, D.; Park, J. V.; Soll, L. Journal of Bacteriology, Vol. 145, Issue 2 https://doi.org/10.1128/JB.145.2.704-712.1981	journal	January 1981
Quadruplet codons: implications for code expansion and the specification of translation step size Moore, Barry; Persson, Britt C.; Nelson, Chad C. Journal of Molecular Biology, Vol. 298, Issue 2 https://doi.org/10.1006/jmbi.2000.3658	journal	April 2000
Progress toward the evolution of an organism with an expanded genetic code Liu, David R.; Schultz, Peter G. Proceedings of the National Academy of Sciences, Vol. 96, Issue 9, p. 4780-4785 https://doi.org/10.1073/pnas.96.9.4780	journal	April 1999
Enzymatic incorporation of a new base pair into DNA and RNA extends the genetic alphabet Piccirilli, Joseph A.; Benner, Steven A.; Krauch, Tilman Nature, Vol. 343, Issue 6253 https://doi.org/10.1038/343033a0	journal	January 1990
Construction of Escherichia coli amber suppressor tRNA genes: II. Synthesis of additional tRNA genes and improvement of suppressor efficiency Kleina, Lynn G.; Masson, Jean-Michel; Normanly, Jennifer Journal of Molecular Biology, Vol. 213, Issue 4, p. 705-717 https://doi.org/10.1016/S0022-2836(05)80257-8	journal	June 1990
Editing of errors in selection of amino acids for protein synthesis. Jakubowski, H.; Goldman, E. Microbiological Reviews, Vol. 56, Issue 3 https://doi.org/10.1128/MMBR.56.3.412-429.1992	journal	January 1992
Genetic code in evolution: switching species-specific aminoacylation with a peptide transplant Wakasugi, K. The EMBO Journal, Vol. 17, Issue 1 https://doi.org/10.1093/emboj/17.1.297	journal	January 1998
Incorporation of Trifluoromethionine into a Phage Lysozyme: Implications and a New Marker for Use in Protein ¹⁹ F NMR ^† Duewel, Henry; Daub, Elisabeth; Robinson, Valerie Biochemistry, Vol. 36, Issue 11 https://doi.org/10.1021/bi9617973	journal	March 1997
An Engineered Tetrahymena tRNA ^Gln for in Vivo Incorporation of Unnatural Amino Acids into Proteins by Nonsense Suppression Saks, Margaret E.; Sampson, Jeffrey R.; Nowak, Mark W. Journal of Biological Chemistry, Vol. 271, Issue 38 https://doi.org/10.1074/jbc.271.38.23169	journal	September 1996
Specific Covalent Labeling of Recombinant Protein Molecules Inside Live Cells Griffin, B. Albert; Adams, Stephen R.; Tsien, Roger Y. Science, Vol. 281, Issue 5374, p. 269-272 https://doi.org/10.1126/science.281.5374.269	journal	July 1998
2 .ANG. Resolution Structure of DppA, a Periplasmic Dipeptide Transport/Chemosensory Receptor Nickitenko, Alexei V.; Trakhanov, Sergei; Quiocho, Florante A. Biochemistry, Vol. 34, Issue 51 https://doi.org/10.1021/bi00051a006	journal	December 1995
Enzyme-generated intracellular fluorescence for single-cell reporter gene analysis utilizing Escherichia coli-glucuronidase Lorincz, Matthew; Roederer, Mario; Diwu, Zhenjun Cytometry, Vol. 24, Issue 4, p. 321-329 https://doi.org/10.1002/(SICI)1097-0320(19960801)24:4<321::AID-CYTO3>3.0.CO;2-I	journal	August 1996
Biodegradation of Aromatic Compounds by Escherichia coli Diaz, E.; Ferrandez, A.; Prieto, M. A. Microbiology and Molecular Biology Reviews, Vol. 65, Issue 4 https://doi.org/10.1128/MMBR.65.4.523-569.2001	journal	December 2001
Differences in Backbone Structure between Angiotensin II Agonists and Type I Antagonists Matsoukas, John M.; Agelis, George; Wahhab, Amal Journal of Medicinal Chemistry, Vol. 38, Issue 23 https://doi.org/10.1021/jm00023a005	journal	November 1995
Engineering a tRNA and aminoacyl-tRNA synthetase for the site-specific incorporation of unnatural amino acids into proteins in vivo Liu, D. R.; Magliery, T. J.; Pastrnak, M. Proceedings of the National Academy of Sciences, Vol. 94, Issue 19 https://doi.org/10.1073/pnas.94.19.10092	journal	September 1997
Protein Engineering by In Vivo Incorporation of Non-Natural Amino Acids: Control of Incorporation of Methionine Analogues by Methionyl-tRNA Synthetase Kiick, Kristi L.; Tirrell, David A. Tetrahedron, Vol. 56, Issue 48, p. 9487-9493 https://doi.org/10.1016/S0040-4020(00)00833-4	journal	November 2000
Enlarging the Amino Acid Set of Escherichia coli by Infiltration of the Valine Coding Pathway Doring, V.; Mootz, H. D.; Nangle, L. A. Science, Vol. 292, Issue 5516 https://doi.org/10.1126/science.1057718	journal	April 2001
Site-Directed Mutagenesis with an Expanded Genetic Code Mendel, D.; Cornish, V. W.; Schultz, P. G. Annual Review of Biophysics and Biomolecular Structure, Vol. 24, Issue 1 https://doi.org/10.1146/annurev.bb.24.060195.002251	journal	June 1995
A synthetic IgG-binding domain based on staphylococcal protein A Nilsson, Björn; Moks, Tomas; Jansson, Birger "Protein Engineering, Design and Selection", Vol. 1, Issue 2 https://doi.org/10.1093/protein/1.2.107	journal	January 1987
Incorporation of Two Different Nonnatural Amino Acids Independently into a Single Protein through Extension of the Genetic Code Hohsaka, Takahiro; Ashizuka, Yuki; Sasaki, Hiroshi Journal of the American Chemical Society, Vol. 121, Issue 51 https://doi.org/10.1021/ja992204p	journal	December 1999
Co-Expression of Yeast Amber Suppressor tRNATyr and Tyrosyl-tRNA Synthetase in Escherichia coli: Possibility to Expand the Genetic Code Ohno, S.; Yokogawa, T.; Fujii, I. Journal of Biochemistry, Vol. 124, Issue 6 https://doi.org/10.1093/oxfordjournals.jbchem.a022221	journal	December 1998
Substrate Specificity Is Determined by Amino Acid Binding Pocket Size in Escherichia coli Phenylalanyl-tRNA Synthetase Ibba, Michael; Kast, Peter; Hennecke, Hauke Biochemistry, Vol. 33, Issue 23 https://doi.org/10.1021/bi00189a013	journal	June 1994
Biosynthetic site-specific incorporation of a non-natural amino acid into a polypeptide Bain, J. D.; Diala, Edward S.; Glabe, Charles G. Journal of the American Chemical Society, Vol. 111, Issue 20, p. 8013-8014 https://doi.org/10.1021/ja00202a052	journal	September 1989
An expanding genetic code Cropp, T. Ashton; Schultz, Peter G. Trends in Genetics, Vol. 20, Issue 12, p. 625-630 https://doi.org/10.1016/j.tig.2004.09.013	journal	December 2004
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
Residue-specific bioincorporation of non-natural, biologically active amino acids into proteins as possible drug carriers: Structure and stability of the per-thiaproline mutant of annexin V Budisa, N.; Minks, C.; Medrano, F. J. Proceedings of the National Academy of Sciences, Vol. 95, Issue 2 https://doi.org/10.1073/pnas.95.2.455	journal	January 1998
Synthetically modified DNAs as substrates for polymerases Kool, E. Current Opinion in Chemical Biology, Vol. 4, Issue 6, p. 602-608 https://doi.org/10.1016/S1367-5931(00)00141-1	journal	December 2000
Programming peptidomimetic syntheses by translating genetic codes designed de novo Forster, A. C.; Tan, Z.; Nalam, M. N. L. Proceedings of the National Academy of Sciences, Vol. 100, Issue 11, p. 6353-6357 https://doi.org/10.1073/pnas.1132122100	journal	May 2003
Multicolor and Electron Microscopic Imaging of Connexin Trafficking Gaietta, G. Science, Vol. 296, Issue 5567 https://doi.org/10.1126/science.1068793	journal	April 2002
New Photolabeling and Crosslinking Methods Brunner, Josef Annual Review of Biochemistry, Vol. 62, Issue 1 https://doi.org/10.1146/annurev.bi.62.070193.002411	journal	June 1993
Probing ion permeation and gating in a K+ channel with backbone mutations in the selectivity filter Lu, Tao; Ting, Alice Y.; Mainland, Joel Nature Neuroscience, Vol. 4, Issue 3 https://doi.org/10.1038/85080	journal	March 2001
Transmembrane protein structure: spin labeling of bacteriorhodopsin mutants Altenbach, C.; Marti, T.; Khorana, H. Science, Vol. 248, Issue 4959 https://doi.org/10.1126/science.2160734	journal	June 1990
Universal rules and idiosyncratic features in tRNA identity Giege, R.; Sissler, M.; Florentz, C. Nucleic Acids Research, Vol. 26, Issue 22 https://doi.org/10.1093/nar/26.22.5017	journal	November 1998
Structure of T7 RNA polymerase complexed to the transcriptional inhibitor T7 lysozyme Jeruzalmi, David; Steitz, Thomas A. The EMBO Journal, Vol. 17, Issue 14 https://doi.org/10.1093/emboj/17.14.4101	journal	July 1998
Absolute configuration of the enantiomers of 7-chloro-4-[[4-(diethylamino)-1-methylbutyl]amino]quinoline (chloroquine) Craig, J. Cymerman; Bhargava, Hemendra N.; Everhart, E. Thomas The Journal of Organic Chemistry, Vol. 53, Issue 6, p. 1167-1170 https://doi.org/10.1021/jo00241a009	journal	March 1988
Novel cofactors via post-translational modifications of enzyme active sites Okeley, Nicole M.; van der Donk, Wilfred A. Chemistry & Biology, Vol. 7, Issue 7 https://doi.org/10.1016/S1074-5521(00)00140-X	journal	July 2000
Site-Specific Protein Modification Using a Ketone Handle Cornish, Virginia W.; Hahn, Klaus M.; Schultz, Peter G. Journal of the American Chemical Society, Vol. 118, Issue 34, p. 8150-8151 https://doi.org/10.1021/ja961216x	journal	January 1996
Nicotinic receptor binding site probed with unnatural amino acid incorporation in intact cells Nowak, M.; Kearney, P. Science, Vol. 268, Issue 5209 https://doi.org/10.1126/science.7716551	journal	April 1995
Probing Protein Structure and Function with an Expanded Genetic Code Cornish, Virginia W.; Mendel, David; Schultz, Peter G. Angewandte Chemie International Edition in English, Vol. 34, Issue 6, p. 621-633 https://doi.org/10.1002/anie.199506211	journal	March 1995
Directed evolution of the site specificity of Cre recombinase Santoro, S. W.; Schultz, P. G. Proceedings of the National Academy of Sciences, Vol. 99, Issue 7, p. 4185-4190 https://doi.org/10.1073/pnas.022039799	journal	March 2002
Studying organelle physiology with fusion protein-targeted avidin and fluorescent biotin conjugates Wu, Minnie M.; Llopis, Juan; Adams, Stephen R. Methods in Enzymology https://doi.org/10.1016/S0076-6879(00)27301-1	book	January 2000
Site-directed conjugation of nonpeptide groups to peptides and proteins via periodate oxidation of a 2-amino alcohol. Application to modification at N-terminal serine Geoghegan, Kieran F.; Stroh, Justin G. Bioconjugate Chemistry, Vol. 3, Issue 2 https://doi.org/10.1021/bc00014a008	journal	March 1992
A New Strategy for the Site-Specific Modification of Proteins in Vivo Zhang, Zhiwen; Smith, Brian A. C.; Wang, Lei Biochemistry, Vol. 42, Issue 22, p. 6735-6746 https://doi.org/10.1021/bi0300231	journal	June 2003
Highly Precise Shape Mimicry by a Difluorotoluene Deoxynucleoside, a Replication-Competent Substitute for Thymidine Guckian, Kevin M.; Kool, Eric T. Angewandte Chemie International Edition in English, Vol. 36, Issue 24, p. 2825-2828 https://doi.org/10.1002/anie.199728251	journal	January 1997
Site-specific incorporation of biotinylated amino acids to identify surface-exposed residues in integral membrane proteins Gallivan, Justin P.; Lester, Henry A.; Dougherty, Dennis A. Chemistry & Biology, Vol. 4, Issue 10, p. 739-749 https://doi.org/10.1016/S1074-5521(97)90312-4	journal	October 1997
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
Structure of tyrosyl-tRNA synthetase refined at 2.3 Å resolution: Interaction of the enzyme with the tyrosyl adenylate intermediate Brick, P.; Bhat, T. N.; Blow, D. M. Journal of Molecular Biology, Vol. 208, Issue 1, p. 83-98 https://doi.org/10.1016/0022-2836(89)90090-9	journal	July 1989
Major Anticodon-binding Region Missing from an Archaebacterial tRNA Synthetase Steer, Brian A.; Schimmel, Paul Journal of Biological Chemistry, Vol. 274, Issue 50 https://doi.org/10.1074/jbc.274.50.35601	journal	December 1999
A Novel Copper-Mediated DNA Base Pair Meggers, Eric; Holland, Patrick L.; Tolman, William B. Journal of the American Chemical Society, Vol. 122, Issue 43, p. 10714-10715 https://doi.org/10.1021/ja0025806	journal	November 2000
Backbone Mutations in Transmembrane Domains of a Ligand-Gated Ion Channel England, Pamela M.; Zhang, Yinong; Dougherty, Dennis A. Cell, Vol. 96, Issue 1, p. 89-98 https://doi.org/10.1016/S0092-8674(00)80962-9	journal	January 1999
Strategies for in vitro and in vivo translation with non-natural amino acids Ibba, Michael Biotechnology and Genetic Engineering Reviews, Vol. 13, Issue 1 https://doi.org/10.1080/02648725.1996.10647929	journal	December 1996
A New Functional Suppressor tRNA/Aminoacyl−tRNA Synthetase Pair for the in Vivo Incorporation of Unnatural Amino Acids into Proteins Wang, Lei; Magliery, Thomas J.; Liu, David R. Journal of the American Chemical Society, Vol. 122, Issue 20, p. 5010-5011 https://doi.org/10.1021/ja000595y	journal	May 2000
Efforts toward Expansion of the Genetic Alphabet: DNA Polymerase Recognition of a Highly Stable, Self-Pairing Hydrophobic Base McMinn, Dustin L.; Ogawa, Anthony K.; Wu, Yiqin Journal of the American Chemical Society, Vol. 121, Issue 49 https://doi.org/10.1021/ja9925150	journal	December 1999
Quisqualic acid analogs: synthesis of .beta.-heterocyclic 2-aminopropanoic acid derivatives and their activity at a novel quisqualate-sensitized site Subasinghe, Nalin; Schulte, Marvin; Roon, Robert J. Journal of Medicinal Chemistry, Vol. 35, Issue 24 https://doi.org/10.1021/jm00102a014	journal	November 1992
Noninvasive Tracing of Recombinant Proteins with “Fluorophenylalanine-Fingers” Minks, Caroline; Huber, Robert; Moroder, Luis Analytical Biochemistry, Vol. 284, Issue 1 https://doi.org/10.1006/abio.2000.4667	journal	August 2000
Libraries of hybrid proteins from distantly related sequences Sieber, Volker; Martinez, Carlos A.; Arnold, Frances H. Nature Biotechnology, Vol. 19, Issue 5 https://doi.org/10.1038/88129	journal	May 2001
5′–3′ Exonucleases in phosphorothioate-based oligonucleotide-directed mutagenesis Sayers, Jon R.; Schmidt, Walter; Eckstein, Fritz Nucleic Acids Research, Vol. 16, Issue 3 https://doi.org/10.1093/nar/16.3.791	journal	January 1988
Compilation of tRNA sequences and sequences of tRNA genes Sprinzl, Mathias; Horn, Carsten; Brown, Melissa Nucleic Acids Research, Vol. 26, Issue 1, p. 148-153 https://doi.org/10.1093/nar/26.1.148	journal	January 1998
Glycine tRNA mutants with normal anticodon loop size cause -1 frameshifting. O'Mahony, D. J.; Mims, B. H.; Thompson, S. Proceedings of the National Academy of Sciences, Vol. 86, Issue 20 https://doi.org/10.1073/pnas.86.20.7979	journal	October 1989
A general method for site-specific incorporation of unnatural amino acids into proteins Noren, C.; Anthony-Cahill, S.; Griffith, M. Science, Vol. 244, Issue 4901 https://doi.org/10.1126/science.2649980	journal	April 1989
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 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
Enzymatic Phosphorylation of Unnatural Nucleosides Wu, Yiqin; Fa, Ming; Tae, Eunju Lee Journal of the American Chemical Society, Vol. 124, Issue 49 https://doi.org/10.1021/ja028050m	journal	December 2002
Bioincorporation of telluromethionine into proteins: a promising new approach for X-ray structure analysis of proteins Budisa, Nediljko; Karnbrock, Wilhelm; Steinbacher, Stefan Journal of Molecular Biology, Vol. 270, Issue 4, p. 616-623 https://doi.org/10.1006/jmbi.1997.1132	journal	July 1997
Production and fluorescence-activated cell sorting of Escherichia coli expressing a functional antibody fragment on the external surface. Francisco, J. A.; Campbell, R.; Iverson, B. L. Proceedings of the National Academy of Sciences, Vol. 90, Issue 22 https://doi.org/10.1073/pnas.90.22.10444	journal	November 1993
Efficient introduction of alkene functionality into proteins in vivo van Hest, Jan C. M.; Tirrell, David A. FEBS Letters, Vol. 428, Issue 1-2, p. 68-70 https://doi.org/10.1016/S0014-5793(98)00489-X	journal	May 1998
Enzymatic incorporation of a new base pair into DNA and RNA Switzer, Christopher; Moroney, Simon E.; Benner, Steven A. Journal of the American Chemical Society, Vol. 111, Issue 21, p. 8322-8323 https://doi.org/10.1021/ja00203a067	journal	October 1989
Major tyrosine identity determinants in Methanococcus jannaschii and Saccharomyces cerevisiae tRNA ^Tyr are conserved but expressed differently : tRNA identity for Fechter, Pierre; Rudinger-Thirion, Joëlle; Tukalo, Mikhail European Journal of Biochemistry, Vol. 268, Issue 3 https://doi.org/10.1046/j.1432-1327.2001.01931.x	journal	February 2001
Fluorinated Coiled-Coil Proteins Prepared In Vivo Display Enhanced Thermal and Chemical Stability Tang, Yi; Ghirlanda, Giovanna; Petka, Wendy A. Angewandte Chemie International Edition, Vol. 40, Issue 8, p. 1494-1496 https://doi.org/10.1002/1521-3773(20010417)40:8<1494::AID-ANIE1494>3.0.CO;2-X	journal	April 2001
693. A new synthesis of glutamine and of γ-dipeptides of glutamic acid from phthalylated intermediates King, F. E.; Kidd, D. A. A. J. Chem. Soc., Vol. 0, Issue 0 https://doi.org/10.1039/JR9490003315	journal	January 1949
Toward the experimental codon reassignment in vivo : protein building with an expanded amino acid repertoire Budisa, Nediljko; Minks, Caroline; Alefelder, Stefan The FASEB Journal, Vol. 13, Issue 1 https://doi.org/10.1096/fasebj.13.1.41	journal	January 1999
Exploring the Limits of Codon and Anticodon Size Anderson, J. Christopher; Magliery, Thomas J.; Schultz, Peter G. Chemistry & Biology, Vol. 9, Issue 2, p. 237-244 https://doi.org/10.1016/S1074-5521(02)00094-7	journal	February 2002
Crystal structure of the dipeptide binding protein from Escherichia coli involved in active transport and chemotaxis Dunten, Pete; Mowbray, Sherry L. Protein Science, Vol. 4, Issue 11 https://doi.org/10.1002/pro.5560041110	journal	November 1995
Efficient introduction of aryl bromide functionality into proteins in vivo Sharma, Nandita; Furter, Rolf; Kast, Peter FEBS Letters, Vol. 467, Issue 1, p. 37-40 https://doi.org/10.1016/S0014-5793(00)01120-0	journal	February 2000
Fluorescent Protein Biosensors: Measurement of Molecular Dynamics in Living Cells Giuliano, K. A.; Post, P. L.; Hahn, K. M. Annual Review of Biophysics and Biomolecular Structure, Vol. 24, Issue 1 https://doi.org/10.1146/annurev.bb.24.060195.002201	journal	June 1995
Protein-protein interaction: a genetic selection for compensating mutations at the barnase-barstar interface. Jucovic, M.; Hartley, R. W. Proceedings of the National Academy of Sciences, Vol. 93, Issue 6 https://doi.org/10.1073/pnas.93.6.2343	journal	March 1996
Phage selection for site-specific incorporation of unnatural amino acids into proteins in vivo Pastrnak, M. Bioorganic & Medicinal Chemistry, Vol. 9, Issue 9, p. 2373-2379 https://doi.org/10.1016/S0968-0896(01)00157-2	journal	September 2001
Quantitation of Transcription and Clonal Selection of Single Living Cells with -Lactamase as Reporter Zlokarnik, G. Science, Vol. 279, Issue 5347 https://doi.org/10.1126/science.279.5347.84	journal	January 1998
A New UAG-Encoded Residue in the Structure of a Methanogen Methyltransferase Hao, B. Science, Vol. 296, Issue 5572 https://doi.org/10.1126/science.1069556	journal	May 2002
Addition of a photocrosslinking amino acid to the genetic code of Escherichia coli Chin, J. W.; Martin, A. B.; King, D. S. Proceedings of the National Academy of Sciences, Vol. 99, Issue 17, p. 11020-11024 https://doi.org/10.1073/pnas.172226299	journal	August 2002
Efficient Incorporation of Nonnatural Amino Acids with Large Aromatic Groups into Streptavidin in In Vitro Protein Synthesizing Systems Hohsaka, Takahiro; Kajihara, Daisuke; Ashizuka, Yuki Journal of the American Chemical Society, Vol. 121, Issue 1 https://doi.org/10.1021/ja9813109	journal	January 1999
Expanding the genetic code: selection of efficient suppressors of four-base codons and identification of “shifty” four-base codons with a library approach in Escherichia coli Magliery, Thomas J.; Anderson, J. Christopher; Schultz, Peter G. Journal of Molecular Biology, Vol. 307, Issue 3, p. 755-769 https://doi.org/10.1006/jmbi.2001.4518	journal	March 2001
Synthesis of novel α-amino-acids and derivatives using radical chemistry: synthesis of L- and D-α-amino-adipic acids, L-α Barton, Derek H. R.; Hervé, Yolande; Potier, Pierre Tetrahedron, Vol. 43, Issue 19, p. 4297-4308 https://doi.org/10.1016/S0040-4020(01)90305-9	journal	January 1987
Aminoacyl-tRNA synthetases: Versatile players in the changing theater of translation Francklyn, Christopher; Perona, John J.; Puetz, Joern RNA, Vol. 8, Issue 11 https://doi.org/10.1017/S1355838202021180	journal	November 2002
High-level Biosynthetic Substitution of Methionine in Proteins by its Analogs 2-Aminohexanoic Acid, Selenomethionine, Telluromethionine and Ethionine in Escherichia coli Budisa, Nediljko; Steipe, Boris; Demange, Pascal European Journal of Biochemistry, Vol. 230, Issue 2 https://doi.org/10.1111/j.1432-1033.1995.tb20622.x	journal	June 1995
A binding protein for l-glutamine and its relation to active transport in E. coli Weiner, Joel H.; Furlong, Clement E.; Heppel, Leon A. Archives of Biochemistry and Biophysics, Vol. 142, Issue 2, p. 715-717 https://doi.org/10.1016/0003-9861(71)90538-8	journal	February 1971
Novel Biological Process for L-DOPA Production from L-Tyrosine by P-Hydroxyphenylacetate 3-Hydroxylase Lee, Jang-Young; Xun, Luying Biotechnology Letters, Vol. 20, Issue 5, p. 479-482 https://doi.org/10.1023/A:1005440229420	journal	January 1998
[5]Disulfide bonds as probes of protein folding pathways Creighton, Thomas E. Methods in Enzymology https://doi.org/10.1016/0076-6879(86)31036-X	book	January 1986
A Mutant Escherichia coli Tyrosyl-tRNA Synthetase Utilizes the Unnatural Amino Acid Azatyrosine More Efficiently than Tyrosine Hamano-Takaku, Fumie; Iwama, Toshiharu; Saito-Yano, Shio Journal of Biological Chemistry, Vol. 275, Issue 51, p. 40324-40328 https://doi.org/10.1074/jbc.M003696200	journal	September 2000
Expanding the genetic code Wang, Lei; Schultz, Peter G. Chemical Communications, Issue 1 https://doi.org/10.1039/b108185n	journal	December 2001
Efficient Incorporation of Unsaturated Methionine Analogues into Proteins in Vivo van Hest, Jan C. M.; Kiick, Kristi L.; Tirrell, David A. Journal of the American Chemical Society, Vol. 122, Issue 7 https://doi.org/10.1021/ja992749j	journal	February 2000
Translational efficiency of transfer RNA's: uses of an extended anticodon Yarus, M. Science, Vol. 218, Issue 4573 https://doi.org/10.1126/science.6753149	journal	November 1982
Synthesis of optically pure pipecolates from L-asparagine. Application to the total synthesis of (+)-apovincamine through amino acid decarbonylation and iminium ion cyclization Christie, Bradley D.; Rapoport, Henry The Journal of Organic Chemistry, Vol. 50, Issue 8 https://doi.org/10.1021/jo00208a017	journal	April 1985
Aspartate identity of transfer RNAs Giegé, R.; Florentz, C.; Kern, D. Biochimie, Vol. 78, Issue 7, p. 605-623 https://doi.org/10.1016/S0300-9084(96)80007-1	journal	January 1996
Characterization of an ‘orthogonal’ suppressor tRNA derived from E. coli tRNA₂^Gln Liu, David R.; Magliery, Thomas J.; Schultz, Peter G. Chemistry & Biology, Vol. 4, Issue 9, p. 685-691 https://doi.org/10.1016/S1074-5521(97)90224-6	journal	September 1997
The gene cluster for chloramphenicol biosynthesis in Streptomyces venezuelae ISP5230 includes novel shikimate pathway homologues and a monomodular non-ribosomal peptide synthetase gene Piraee, M.; Magarvey, N.; He, J. Microbiology, Vol. 147, Issue 10 https://doi.org/10.1099/00221287-147-10-2817	journal	October 2001
Efforts toward the Expansion of the Genetic Alphabet: Information Storage and Replication with Unnatural Hydrophobic Base Pairs Ogawa, Anthony K.; Wu, Yiqin; McMinn, Dustin L. Journal of the American Chemical Society, Vol. 122, Issue 14 https://doi.org/10.1021/ja9940064	journal	April 2000
Glutamine analogues as potential antimalarials Azoulay, M.; Vilmont, M.; Frappier, F. European Journal of Medicinal Chemistry, Vol. 26, Issue 2, p. 201-205 https://doi.org/10.1016/0223-5234(91)90030-Q	journal	March 1991
Crystal structure of yeast phenylalanine transfer RNA: I. Crystallographic refinement Sussman, Joel L.; Holbrook, Stephen R.; Warrant, R. Wade Journal of Molecular Biology, Vol. 123, Issue 4, p. 607-630 https://doi.org/10.1016/0022-2836(78)90209-7	journal	August 1978
Exploiting unassigned codons in Micrococcus luteus for tRNA-based amino acid mutagenesis Kowal, A. Nucleic Acids Research, Vol. 25, Issue 22 https://doi.org/10.1093/nar/25.22.4685	journal	November 1997
Synthesis of Derivatives of Glutamine as Model Substrates for Anti-tumor Agents Friedman, Orrie M.; Chatterji, Ramesh Journal of the American Chemical Society, Vol. 81, Issue 14, p. 3750-3752 https://doi.org/10.1021/ja01523a064	journal	July 1959
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
Rescuing an essential enzyme-RNA complex with a non-essential appended domain Whelihan, E. F. The EMBO Journal, Vol. 16, Issue 10 https://doi.org/10.1093/emboj/16.10.2968	journal	May 1997
Expansion of the genetic code: Site-directed p-fluoro-phenylalanine incorporation in Escherichia coli Furter, Rolf Protein Science, Vol. 7, Issue 2, p. 419-426 https://doi.org/10.1002/pro.5560070223	journal	February 1998

Similar Records

Site specific incorporation of keto amino acids into proteins

Patent · Tue Oct 07 00:00:00 EDT 2008 · OSTI ID:1034342

Schultz, Peter G; Wang, Lei

Site specific incorporation of keto amino acids into proteins

Patent · Tue Mar 22 00:00:00 EDT 2011 · OSTI ID:1034342

Schultz, Peter G; Wang, Lei

Site specific incorporation of keto amino acids into proteins

Patent · Tue Feb 14 00:00:00 EST 2012 · OSTI ID:1034342

Schultz, Peter G; Wang, Lei

Related Subjects

59 BASIC BIOLOGICAL SCIENCES

Title: Site specific incorporation of keto amino acids into proteins

Citation Formats

References (132)

Similar Records

Related Subjects