Selective posttranslational modification of phage-displayed polypeptides
Abstract
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.
- Inventors:
- Issue Date:
- Research Org.:
- The Scripps Research Inst., La Jolla, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1083220
- Patent Number(s):
- 8367588
- Application Number:
- 11/992,341
- Assignee:
- The Scripps Research Institute (La Jolla, CA)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07K - PEPTIDES
C - CHEMISTRY C12 - BIOCHEMISTRY C12N - MICROORGANISMS OR ENZYMES
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES
Citation Formats
Tsao, Meng-Lin, Tian, Feng, and Schultz, Peter. Selective posttranslational modification of phage-displayed polypeptides. United States: N. p., 2013.
Web.
Tsao, Meng-Lin, Tian, Feng, & Schultz, Peter. Selective posttranslational modification of phage-displayed polypeptides. United States.
Tsao, Meng-Lin, Tian, Feng, and Schultz, Peter. Tue .
"Selective posttranslational modification of phage-displayed polypeptides". United States. https://www.osti.gov/servlets/purl/1083220.
@article{osti_1083220,
title = {Selective posttranslational modification of phage-displayed polypeptides},
author = {Tsao, Meng-Lin and Tian, Feng and Schultz, Peter},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Feb 05 00:00:00 EST 2013},
month = {Tue Feb 05 00:00:00 EST 2013}
}
Works referenced in this record:
Glycoprotein synthesis
patent, August 2005
- Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen
- US Patent Document 6,927,042
In vivo incorporation of unnatural amino acids
patent, May 2006
- Schultz, Peter G.; Wang, Lei; Anderson, John Christopher
- US Patent Document 7,045,337
Methods and compositions for the production of orthogonal tRNA-aminoacyl tRNA synthetase pairs
patent, August 2006
- Schultz, Peter G.; Wang, Lei; Anderson, John Christopher
- US Patent Document 7,083,970
Glycoprotein synthesis
patent, February 2007
- Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen
- US Patent Document 7,183,082
Glycoprotein synthesis
patent, April 2007
- Shultz, Peter G.; Wang, Lei; Zhang, Zhiwen
- US Patent Document 7,199,222
Glycoprotein synthesis
patent, May 2007
- Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen
- US Patent Document 7,217,809
Glycoprotein synthesis
patent, July 2007
- Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen
- US Patent Document 7,238,510
Glycoprotein synthesis
patent, August 2007
- Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen
- US Patent Document 7,262,040
An expanded genetic code with a functional quadruplet codon
journal, May 2004
- Anderson, J. C.; Wu, N.; Santoro, S. W.
- Proceedings of the National Academy of Sciences, Vol. 101, Issue 20, p. 7566-7571
Biosynthetic site-specific incorporation of a non-natural amino acid into a polypeptide
journal, September 1989
- Bain, J. D.; Diala, Edward S.; Glabe, Charles G.
- Journal of the American Chemical Society, Vol. 111, Issue 20, p. 8013-8014
Addition of a photocrosslinking amino acid to the genetic code of Escherichia coli
journal, August 2002
- Chin, J. W.; Martin, A. B.; King, D. S.
- Proceedings of the National Academy of Sciences, Vol. 99, Issue 17, p. 11020-11024
Addition of p-Azido-L -phenylalanine to the Genetic Code of Escherichia coli
journal, July 2002
- Chin, Jason W.; Santoro, Stephen W.; Martin, Andrew B.
- Journal of the American Chemical Society, Vol. 124, Issue 31, p. 9026-9027
An Expanded Eukaryotic Genetic Code
journal, August 2003
- Chin, Jason W.; Cropp, T. Ashton; Anderson, J. Christopher
- Science, Vol. 301, Issue 5635, p. 964-967
In vivo incorporation of an alkyne into proteins in Escherichia coli
journal, March 2005
- Deiters, Alexander; Schultz, Peter G.
- Bioorganic & Medicinal Chemistry Letters, Vol. 15, Issue 5, p. 1521-1524
Adding Amino Acids with Novel Reactivity to the Genetic Code of Saccharomyces Cerevisiae
journal, October 2003
- Deiters, Alexander; Cropp, T. Ashton; Mukherji, Mridul
- Journal of the American Chemical Society, Vol. 125, Issue 39, p. 11782-11783
[15] Biosynthetic method for introducing unnatural amino acids site-specifically into proteins
book, January 1991
- Ellman, Jon; Mendel, David; Anthony-Cahill, Spencer
- Molecular Design and Modeling: Concepts and Applications Part A: Proteins, Peptides, and Enzymes, p. 301-336
An unnatural base pair for incorporating amino acid analogs into proteins
journal, February 2002
- Hirao, Ichiro; Ohtsuki, Takashi; Fujiwara, Tsuyoshi
- Nature Biotechnology, Vol. 20, Issue 2
Incorporation of non-natural amino acids into proteins
journal, December 2002
- Hohsaka, Takahiro; Sisido, Masahiko
- Current Opinion in Chemical Biology, Vol. 6, Issue 6
Incorporation of azides into recombinant proteins for chemoselective modification by the Staudinger ligation
journal, December 2001
- Kiick, K. L.; Saxon, E.; Tirrell, D. A.
- Proceedings of the National Academy of Sciences, Vol. 99, Issue 1, p. 19-24
Chemoselective ligation reactions with proteins, oligosaccharides and cells
journal, December 1998
- Lemieux, George A.; Bertozzi, Carolyn R.
- Trends in Biotechnology, Vol. 16, Issue 12, p. 506-513
In Vitro Selection of mRNA Display Libraries Containing an Unnatural Amino Acid
journal, August 2002
- Li, Shuwei; Millward, Steven; Roberts, Richard
- Journal of the American Chemical Society, Vol. 124, Issue 34
A Method for the Generation of Glycoprotein Mimetics
journal, February 2003
- Liu, Haitian; Wang, Lei; Brock, Ansgar
- Journal of the American Chemical Society, Vol. 125, Issue 7
A general method for site-specific incorporation of unnatural amino acids into proteins
journal, April 1989
- Noren, C.; Anthony-Cahill, S.; Griffith, M.
- Science, Vol. 244, Issue 4901
Phage selection for site-specific incorporation of unnatural amino acids into proteins in vivo
journal, September 2001
- Pastrnak, M.
- Bioorganic & Medicinal Chemistry, Vol. 9, Issue 9, p. 2373-2379
Chemical remodelling of cell surfaces in living animals
journal, August 2004
- Prescher, Jennifer A.; Dube, Danielle H.; Bertozzi, Carolyn R.
- Nature, Vol. 430, Issue 7002, p. 873-877
A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective “Ligation” of Azides and Terminal Alkynes
journal, July 2002
- Rostovtsev, Vsevolod V.; Green, Luke G.; Fokin, Valery V.
- Angewandte Chemie International Edition, Vol. 41, Issue 14, p. 2596-2599
Phage Display of Selenopeptides
journal, February 2000
- Sandman, Karen E.; Benner, Jack S.; Noren, Christopher J.
- Journal of the American Chemical Society, Vol. 122, Issue 5
Cell Surface Engineering by a Modified Staudinger Reaction
journal, March 2000
- Saxon, E.
- Science, Vol. 287, Issue 5460
Phage Display
journal, April 1997
- Smith, George P.; Petrenko, Valery A.
- Chemical Reviews, Vol. 97, Issue 2
A Phage Display System with Unnatural Amino Acids
journal, December 2004
- Tian, Feng; Tsao, Meng-Lin; Schultz, Peter G.
- Journal of the American Chemical Society, Vol. 126, Issue 49
Peptidotriazoles on Solid Phase [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
journal, May 2002
- Tornøe, Christian W.; Christensen, Caspar; Meldal, Morten
- The Journal of Organic Chemistry, Vol. 67, Issue 9, p. 3057-3064
Expanding the Genetic Code
journal, January 2005
- Wang, Lei; Schultz, Peter G.
- Angewandte Chemie International Edition, Vol. 44, Issue 1, p. 34-66
Expanding the Genetic Code of Escherichia coli
journal, April 2001
- Wang, L.; Brock, A.; Herberich, B.
- Science, Vol. 292, Issue 5516, p. 498-500
Addition of the keto functional group to the genetic code of Escherichia coli
journal, December 2002
- Wang, L.; Zhang, Z.; Brock, A.
- Proceedings of the National Academy of Sciences, Vol. 100, Issue 1, p. 56-61
Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition
journal, March 2003
- Wang, Qian; Chan, Timothy R.; Hilgraf, Robert
- Journal of the American Chemical Society, Vol. 125, Issue 11, p. 3192-3193
An expanding genetic code
journal, July 2005
- Xie, Jianming; Schultz, Peter G.
- Methods, Vol. 36, Issue 3, p. 227-238
Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells
journal, June 2004
- Zhang, Zhiwen; Alfonta, Lital; Tian, Feng
- Proceedings of the National Academy of Sciences, Vol. 101, Issue 24
Works referencing / citing this record:
Cell Surface Labeling of Escherichia c oli via Copper(I)-Catalyzed [3+2] Cycloaddition
journal, September 2003
- Link, A. James; Tirrell, David A.
- Journal of the American Chemical Society, Vol. 125, Issue 37