Selective posttranslational modification of phage-displayed polypeptides

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

Title: Selective posttranslational modification of phage-displayed polypeptides

Patent · Tue Feb 05 00:00:00 EST 2013

OSTI ID:1083220

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 Inst., La Jolla, CA (United States)

Sponsoring Organization:: USDOE

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

Patent Number(s):: 8,367,588

Application Number:: 11/992,341

OSTI ID:: 1083220

Country of Publication:: United States

Language:: English

References (38)

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/6927042 US Patent Document 6,927,042	patent	August 2005
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
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
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
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
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
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
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
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
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
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
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 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
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
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
[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
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
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
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
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
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
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
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
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
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
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V. Angewandte Chemie International Edition, Vol. 41, Issue 14, p. 2596-2599 https://doi.org/10.1002/1521-3773(20020715)41:14<2596::AID-ANIE2596>3.0.CO;2-4	journal	July 2002
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
Phage Display Smith, George P.; Petrenko, Valery A. Chemical Reviews, Vol. 97, Issue 2 https://doi.org/10.1021/cr960065d	journal	April 1997
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
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
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
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
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
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
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
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

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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

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