Selective posttranslational modification of phage-displayed polypeptides

Tsao, Meng-Lin; Tian, Feng; Schultz, Peter

Title: Selective posttranslational modification of phage-displayed polypeptides

Patent · Tue Nov 19 00:00:00 EST 2013

OSTI ID:1108941

Tsao, Meng-Lin; Tian, Feng; Schultz, Peter

The invention relates to posttranslational modification of phage-displayed polypeptides. These displayed polypeptides comprise at least one unnatural amino acid, e.g., an aryl-azide amino acid such as p-azido-L-phenylalanine, or an alkynyl-amino acid such as para-propargyloxyphenylalanine, which are incorporated into the phage-displayed fusion polypeptide at a selected position by using an in vivo orthogonal translation system comprising a suitable orthogonal aminoacyl-tRNA synthetase and a suitable orthogonal tRNA species. These unnatural amino acids advantageously provide targets for posttranslational modifications such as azide-alkyne [3+2] cycloaddition reactions and Staudinger modifications.

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Research Organization:: The Scripps Research Institute, La Jolla, CA, USA

Sponsoring Organization:: USDOE

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

Patent Number(s):: 8,586,340

Application Number:: 11/580,223

OSTI ID:: 1108941

Country of Publication:: United States

Language:: English

References (70)

Glycoprotein synthesis Schultz, Peter; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070172915 US Patent Application 11/580203; 20070172915	patent-application	July 2007
Unnatural reactive amino acid genetic code additions Deiters, Alexander; Cropp, T. Ashton; Chin, Jason W. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040265952 US Patent Application 10/826919; 20040265952	patent-application	December 2004
Chemical remodelling of cell surfaces in living animals Prescher, Jennifer A.; Dube, Danielle H.; Bertozzi, Carolyn R. Nature, Vol. 430, Issue 7002, p. 873-877 https://doi.org/10.1038/nature02791	journal	August 2004
Phage Display Smith, George P.; Petrenko, Valery A. Chemical Reviews, Vol. 97, Issue 2 https://doi.org/10.1021/cr960065d	journal	April 1997
A Method for the Generation of Glycoprotein Mimetics Liu, Haitian; Wang, Lei; Brock, Ansgar Journal of the American Chemical Society, Vol. 125, Issue 7 https://doi.org/10.1021/ja029433n	journal	February 2003
Die Erweiterung des genetischen Codes Wang, Lei; Schultz, Peter G. Angewandte Chemie, Vol. 117, Issue 1 https://doi.org/10.1002/ange.200460627	journal	January 2005
Site specific incorporation of keto amino acids into proteins Schultz, Peter G.; Wang, Lei https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060068478 US Patent Application 10/530421; 20060068478	patent-application	March 2006
Engineering M13 for phage display Sidhu, Sachdev S. Biomolecular Engineering, Vol. 18, Issue 2 https://doi.org/10.1016/S1389-0344(01)00087-9	journal	September 2001
Glycoprotein synthesis Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7183082 US Patent Document 7,183,082	patent	February 2007
Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells Zhang, Zhiwen; Alfonta, Lital; Schultz, Peter https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070111193 US Patent Application 10/580987; 20070111193	patent-application	May 2007
Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation Kiick, K. L.; Saxon, E.; Tirrell, D. A. Proceedings of the National Academy of Sciences, Vol. 99, Issue 1, p. 19-24 https://doi.org/10.1073/pnas.012583299	journal	December 2001
Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition Wang, Qian; Chan, Timothy R.; Hilgraf, Robert Journal of the American Chemical Society, Vol. 125, Issue 11, p. 3192-3193 https://doi.org/10.1021/ja021381e	journal	March 2003
Expanding the eukaryotic genetic code Chin, Jason W.; Cropp, T. Ashton; Anderson, J. Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050009049 US Patent Application 10/825867; 20050009049	patent-application	January 2005
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
Compositions of orthogonal leucyl-trna and aminoacyl-trna synthetase pairs and uses thereof Anderson, J. Christopher; Schultz, Peter G. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060160175 US Patent Application 10/563655; 20060160175	patent-application	July 2006
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
Site-specific labeling of proteins for NMR studies Deiters, Alexander; Geierstanger, Bernhard H.; Schultz, Peter G. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060110784 US Patent Application 11/233466; 20060110784	patent-application	May 2006
Site-specific incorporation of redox active amino acids into proteins Alfonta, Lital; Schultz, Peter G.; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050227318 US Patent Application 10/965218; 20050227318	patent-application	October 2005
Glycoprotein synthesis Shultz, Peter G.; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7199222 US Patent Document 7,199,222	patent	April 2007
Site specific incorporation of heavy atom-containing unnatural amino acids into proteins for structure determination Xie, Jianming; Wang, Lei; Wu, Ning https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050272121 US Patent Application 11/137850; 20050272121	patent-application	December 2005
Chemoselective ligation reactions with proteins, oligosaccharides and cells Lemieux, George A.; Bertozzi, Carolyn R. Trends in Biotechnology, Vol. 16, Issue 12, p. 506-513 https://doi.org/10.1016/S0167-7799(98)01230-X	journal	December 1998
Site-specific incorporation of redox active amino acids into proteins Alfonta, Lital; Schultz, Peter G.; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070009990 US Patent Application 10/575991; 20070009990	patent-application	January 2007
Expanding the eukaryotic genetic code Chin, Jason; Cropp, T. Ashton; Anderson, J. Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070166791 US Patent Application 11/710672; 20070166791	patent-application	July 2007
Intermolecular 1,3-Dipolar Cycloadditions Padwa, Albert Comprehensive Organic Synthesis https://doi.org/10.1016/B978-0-08-052349-1.00116-5	book	January 1991
Compositions of orthogonal lysyl-trna and aminoacyl-trna synthetase pairs and uses thereof Anderson, J. Christopher; Wu, Ning; Santoro, Stephen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070042461 US Patent Application 10/563686; 20070042461	patent-application	February 2007
Methods and composition for the production of orthogonal tRNA-aminoacyltRNA synthetase pairs Schultz, Peter; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060234367 US Patent Application 11/254170; 20060234367	patent-application	October 2006
In vivo incorporation of alkynyl amino acids into proteins in eubacteria Deiters, Alexander; Schultz, Peter https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060073507 US Patent Application 11/232425; 20060073507	patent-application	April 2006
[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
Schultz, Peter G.; Wang, Lei https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20040198637 US Patent Application 10/744899; 20040198637	patent-application	October 2004
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
Semisynthesis of Proteins by Expressed Protein Ligation Muir, Tom W. Annual Review of Biochemistry, Vol. 72, Issue 1 https://doi.org/10.1146/annurev.biochem.72.121801.161900	journal	June 2003
Methods and composition for the production of orthogonal tRNA-aminoacyltRNA synthetase pairs Schultz, Peter; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060063244 US Patent Application 11/002387; 20060063244	patent-application	March 2006
An expanding genetic code Xie, Jianming; Schultz, Peter G. Methods, Vol. 36, Issue 3, p. 227-238 https://doi.org/10.1016/j.ymeth.2005.04.010	journal	July 2005
Cell Surface Labeling of Escherichia c oli via Copper(I)-Catalyzed [3+2] Cycloaddition Link, A. James; Tirrell, David A. Journal of the American Chemical Society, Vol. 125, Issue 37 https://doi.org/10.1021/ja036765z	journal	September 2003
ChemInform Abstract: 1,3-DIPOLAR CYCLOADDITION - INTRODUCTION, SURVEY, MECHANISM Huisgen, R. Chemischer Informationsdienst, Vol. 16, Issue 18 https://doi.org/10.1002/chin.198518341	journal	May 1985
Glycoprotein synthesis Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6927042 US Patent Document 6,927,042	patent	August 2005
Compositions of orthogonal lysyl-tRNA and aminoacyl-tRNA synthetase pairs and uses thereof Anderson, J. Christopher; Wu, Ning; Santoro, Stephen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060177900 US Patent Application 11/326970; 20060177900	patent-application	August 2006
Expanding the eukaryotic genetic code Chin, Jason W.; Cropp, T. Ashton; Anderson, J. Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070154952 US Patent Application 11/710655; 20070154952	patent-application	July 2007
Methods and composition for the production of orthogonal tRNA-aminoacyltRNA synthetase pairs Schultz, Peter; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050208536 US Patent Application 11/009635; 20050208536	patent-application	September 2005
Glycoprotein synthesis Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7217809 US Patent Document 7,217,809	patent	May 2007
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
A Phage Display System with Unnatural Amino Acids Tian, Feng; Tsao, Meng-Lin; Schultz, Peter G. Journal of the American Chemical Society, Vol. 126, Issue 49 https://doi.org/10.1021/ja045673m	journal	December 2004
Methods and compositions for the production of orthogonal tRNA-aminoacyl tRNA synthetase pairs Schultz, Peter G.; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7083970 US Patent Document 7,083,970	patent	August 2006
In Vitro Selection of mRNA Display Libraries Containing an Unnatural Amino Acid Li, Shuwei; Millward, Steven; Roberts, Richard Journal of the American Chemical Society, Vol. 124, Issue 34 https://doi.org/10.1021/ja026789q	journal	August 2002
An expanded genetic code with a functional quadruplet codon Anderson, J. C.; Wu, N.; Santoro, S. W. Proceedings of the National Academy of Sciences, Vol. 101, Issue 20, p. 7566-7571 https://doi.org/10.1073/pnas.0401517101	journal	May 2004
Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine Staudinger, H.; Meyer, Jules Helvetica Chimica Acta, Vol. 2, Issue 1, p. 635-646 https://doi.org/10.1002/hlca.19190020164	journal	January 1919
Peptidotriazoles on Solid Phase [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides Tornøe, Christian W.; Christensen, Caspar; Meldal, Morten The Journal of Organic Chemistry, Vol. 67, Issue 9, p. 3057-3064 https://doi.org/10.1021/jo011148j	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
Glycoprotein synthesis Schultz, Peter; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070184517 US Patent Application 11/520849; 20070184517	patent-application	August 2007
Glycoprotein synthesis Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7238510 US Patent Document 7,238,510	patent	July 2007
Phage Display of Selenopeptides Sandman, Karen E.; Benner, Jack S.; Noren, Christopher J. Journal of the American Chemical Society, Vol. 122, Issue 5 https://doi.org/10.1021/ja992462m	journal	February 2000
Cell Surface Engineering by a Modified Staudinger Reaction Saxon, E. Science, Vol. 287, Issue 5460 https://doi.org/10.1126/science.287.5460.2007	journal	March 2000
Adding photoregulated amino acids to the genetic code Deiters, Alexander; Wu, Ning; Schultz, Peter G. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060134746 US Patent Application 11/233508; 20060134746	patent-application	June 2006
Composition of orthogonal glutamyl-trna and aminoacyl-trna synthetase pairs and uses thereof Anderson, J. Christopher; Schultz, Peter G.; Santoro, Stephen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070020634 US Patent Application 10/563656; 20070020634	patent-application	January 2007
Incorporation of non-natural amino acids into proteins Hohsaka, Takahiro; Sisido, Masahiko Current Opinion in Chemical Biology, Vol. 6, Issue 6 https://doi.org/10.1016/S1367-5931(02)00376-9	journal	December 2002
Peptide library and screening method Hart, Charles https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/6107059 US Patent Document 6,107,059	patent	August 2000
Glycoprotein synthesis Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7262040 US Patent Document 7,262,040	patent	August 2007
Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells Zhang, Zhiwen; Alfonta, Lital; Schultz, Peter https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050136513 US Patent Application 11/016348; 20050136513	patent-application	June 2005
Adding Amino Acids with Novel Reactivity to the Genetic Code of Saccharomyces Cerevisiae Deiters, Alexander; Cropp, T. Ashton; Mukherji, Mridul Journal of the American Chemical Society, Vol. 125, Issue 39, p. 11782-11783 https://doi.org/10.1021/ja0370037	journal	October 2003
Expanding the genetic code Wang, Lei; Schultz, Peter G. Chemical Communications, Issue 1 https://doi.org/10.1039/b108185n	journal	December 2001
In vivo incorporation of unnatural amino acids Schultz, Peter G.; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7045337 US Patent Document 7,045,337	patent	May 2006
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
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
Unnatural reactive amino acid genetic code additions Deiters, Alexander; Cropp, T. Ashton; Chin, Jason W. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060246509 US Patent Application 10/561121; 20060246509	patent-application	November 2006
Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells Zhang, Zhiwen; Alfonta, Lital; Tian, Feng Proceedings of the National Academy of Sciences, Vol. 101, Issue 24 https://doi.org/10.1073/pnas.0307029101	journal	June 2004
In vivo incorporation of an alkyne into proteins in Escherichia coli Deiters, Alexander; Schultz, Peter G. Bioorganic & Medicinal Chemistry Letters, Vol. 15, Issue 5, p. 1521-1524 https://doi.org/10.1016/j.bmcl.2004.12.065	journal	March 2005
In vivo site-specific incorporation of N-acetyl-galactosamine amino acids in eubacteria Schultz, Peter G.; Hanson, Sarah R.; Xu, Ran https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060110796 US Patent Application 11/255601; 20060110796	patent-application	May 2006
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

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