Production of carrier-peptide conjugates using chemically reactive unnatural amino acids

Young, Travis; Schultz, Peter G.

Title: Production of carrier-peptide conjugates using chemically reactive unnatural amino acids

Patent · Tue Aug 18 00:00:00 EDT 2015

OSTI ID:1210885

Young, Travis; Schultz, Peter G.

Provided are methods of making carrier polypeptide that include incorporating a first unnatural amino acid into a carrier polypeptide variant, incorporating a second unnatural amino acid into a target polypeptide variant, and reacting the first and second unnatural amino acids to produce the conjugate. Conjugates produced using the provided methods are also provided. In addition, orthogonal translation systems in methylotrophic yeast and methods of using these systems to produce carrier and target polypeptide variants comprising unnatural amino acids are provided.

View Patent

Cite

Export

Save

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

Sponsoring Organization:: USDOE

DOE Contract Number:: FG03-00ER46051

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

Patent Number(s):: 9,109,022

Application Number:: 14/065,111

OSTI ID:: 1210885

Resource Relation:: Patent File Date: 2013 Oct 28

Country of Publication:: United States

Language:: English

References (76)

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
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
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
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
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
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
In vivo incorporation of unnatural amino acids Schultz, Peter; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20050250183 US Patent Application 11/017550; 20050250183	patent-application	November 2005
A strong nitrogen source-regulated promoter for controlled expression of foreign genes in the yeast Pichia pastoris Shen, Shigang; Sulter, Greitje; Jeffries, Thomas W. Gene, Vol. 216, Issue 1, p. 93-102 https://doi.org/10.1016/S0378-1119(98)00315-1	journal	August 1998
Yeast Systems for the Commercial Production of Heterologous Proteins Buckholz, Richard G.; Gleeson, Martin A. G. Bio/Technology, Vol. 9, Issue 11, p. 1067-1072 https://doi.org/10.1038/nbt1191-1067	journal	November 1991
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
Detailed Analysis Concerning the Biodistribution and Metabolism of Human Calcitonin-Derived Cell-Penetrating Peptides Neundorf, I.; Rennert, R.; Franke, J. Bioconjugate Chemistry, Vol. 19, Issue 8, p. 1596-1603 https://doi.org/10.1021/bc800149f	journal	August 2008
Heterologous protein expression in the methylotrophic yeast Pichia pastoris Cereghino, Joan Lin; Cregg, James M. FEMS Microbiology Reviews, Vol. 24, Issue 1, p. 45-66 https://doi.org/10.1111/j.1574-6976.2000.tb00532.x	journal	January 2000
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
Control of protein phosphorylation with a genetically encoded photocaged amino acid Lemke, Edward A.; Summerer, Daniel; Geierstanger, Bernhard H. Nature Chemical Biology, Vol. 3, Issue 12, p. 769-772 https://doi.org/10.1038/nchembio.2007.44	journal	October 2007
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
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
Expression of Foreign Genes in the yeast Pichia pastoris Cereghino, Geoffrey P. Lin; Sunga, Anthony J.; Cereghino, Joan Lin Genetic Engineering: Principles and Methods https://doi.org/10.1007/0-306-47572-3_9	book	January 2001
Adding amino acids to the genetic repertoire Xie, Jianming; Schultz, Peter G. Current Opinion in Chemical Biology, Vol. 9, Issue 6, p. 548-554 https://doi.org/10.1016/j.cbpa.2005.10.011	journal	December 2005
Glycoprotein synthesis Schultz, Peter G.; Wang, Lei; Zhang, Zhiwen https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7129333 US Patent Document 7,129,333	patent	October 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/20070009990 US Patent Application 10/575991; 20070009990	patent-application	January 2007
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
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
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
Systems for the expression of orthogonal translation components in eubacterial host cells Ryu, Youngha; Schultz, Peter https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070281335 US Patent Application 11/715672; 20070281335	patent-application	December 2007
In vivo incorporation of unnatural amino acids Schultz, Peter; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070117184 US Patent Application 11/583551; 20070117184	patent-application	May 2007
Incorporation of Nonnatural Amino Acids Into Proteins Hendrickson, Tamara L.; Crécy-Lagard, Valérie de; Schimmel, Paul Annual Review of Biochemistry, Vol. 73, Issue 1 https://doi.org/10.1146/annurev.biochem.73.012803.092429	journal	June 2004
Optimization of human serum albumin production in methylotrophic yeast Pichia pastoris by repeated fed-batch fermentation Ohya, Tomoshi; Ohyama, Masao; Kobayashi, Kaoru Biotechnology and Bioengineering, Vol. 90, Issue 7, p. 876-887 https://doi.org/10.1002/bit.20507	journal	January 2005
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 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
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
Expanding the Genetic Repertoire of the Methylotrophic Yeast Pichia pastoris Young, Travis S.; Ahmad, Insha; Brock, Ansgar Biochemistry, Vol. 48, Issue 12, p. 2643-2653 https://doi.org/10.1021/bi802178k	journal	March 2009
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
Binding Polypeptides With Diversified And Consensus VH/VL Hypervariable Sequences Dennis, Mark; Liang, Wei-Ching; Wu, Yan https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070160598 US Patent Application 11/557466; 20070160598	patent-application	July 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
Overview of Protein Expression in Pichia pastoris Higgins, David R.; Coligan, John E.; Dunn, Ben M. Current Protocols in Protein Science https://doi.org/10.1002/0471140864.ps0507s02	book	December 1995
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
Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 1: Minimizing misacylation Rodriguez, E. A.; Lester, H. A.; Dougherty, D. A. RNA, Vol. 13, Issue 10 https://doi.org/10.1261/rna.666807	journal	August 2007
Development and Characterization of a Glucagon-Like Peptide 1-Albumin Conjugate: The Ability to Activate the Glucagon-Like Peptide 1 Receptor In Vivo Kim, J. -G.; Baggio, L. L.; Bridon, D. P. Diabetes, Vol. 52, Issue 3 https://doi.org/10.2337/diabetes.52.3.751	journal	March 2003
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
An Improved System for the Generation and Analysis of Mutant Proteins Containing Unnatural Amino Acids in Saccharomyces cerevisiae Chen, Shawn; Schultz, Peter G.; Brock, Ansgar Journal of Molecular Biology, Vol. 371, Issue 1, p. 112-122 https://doi.org/10.1016/j.jmb.2007.05.017	journal	August 2007
Unnatural Amino Acid Incorporation into Virus-Like Particles Strable, Erica; Prasuhn, Duane E.; Udit, Andrew K. Bioconjugate Chemistry, Vol. 19, Issue 4, p. 866-875 https://doi.org/10.1021/bc700390r	journal	April 2008
High-level expression, purification, and characterization of recombinant human tumor necrosis factor synthesized in the methylotrophic yeast Pichia pastoris Sreekrishna, K.; Nelles, Lynn; Potenz, Rica Biochemistry, Vol. 28, Issue 9 https://doi.org/10.1021/bi00435a074	journal	May 1989
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
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
tRNA genes and retroelements in the yeast genome Hani, J. Nucleic Acids Research, Vol. 26, Issue 3 https://doi.org/10.1093/nar/26.3.689	journal	February 1998
Optimization of humanized IgGs in glycoengineered Pichia pastoris Li, Huijuan; Sethuraman, Natarajan; Stadheim, Terrance A. Nature Biotechnology, Vol. 24, Issue 2, p. 210-215 https://doi.org/10.1038/nbt1178	journal	January 2006
Albumin as a drug carrier: Design of prodrugs, drug conjugates and nanoparticles Kratz, Felix Journal of Controlled Release, Vol. 132, Issue 3, p. 171-183 https://doi.org/10.1016/j.jconrel.2008.05.010	journal	December 2008
Recombinant Protein Expression in Pichia pastoris Cregg, James M.; Cereghino, Joan Lin; Shi, Jianying Molecular Biotechnology, Vol. 16, Issue 1 https://doi.org/10.1385/MB:16:1:23	journal	January 2000
PEGylation, successful approach to drug delivery Veronese, Francesco M.; Pasut, Gianfranco Drug Discovery Today, Vol. 10, Issue 21, p. 1451-1458 https://doi.org/10.1016/S1359-6446(05)03575-0	journal	November 2005
Genetically programmed expression of proteins containing the unnatural amino acid phenylselenocysteine Wang, Jiangyun; Schultz, Peter https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070238152 US Patent Application 11/724039; 20070238152	patent-application	October 2007
Nucleophilic Catalysis of Oxime Ligation Dirksen, Anouk; Hackeng, Tilman M.; Dawson, Philip E. Angewandte Chemie International Edition, Vol. 45, Issue 45, p. 7581-7584 https://doi.org/10.1002/anie.200602877	journal	November 2006
Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides Miao, Zhenwei; Liu, Junjie; Norman, Thea https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20060217532 US Patent Application 11/313956; 20060217532	patent-application	September 2006
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
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
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
Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 2: Evaluating suppression efficiency Rodriguez, E. A.; Lester, H. A.; Dougherty, D. A. RNA, Vol. 13, Issue 10 https://doi.org/10.1261/rna.667607	journal	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
Selective posttranslational modification of phage-displayed polypeptides Tsao, Meng-Lin; Tian, Feng; Schultz, Peter https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070178448 US Patent Application 11/580223; 20070178448	patent-application	August 2007
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
Expression of heterologous proteins in Pichia pastoris: a useful experimental tool in protein engineering and production Daly, Rachel; Hearn, Milton T. W. Journal of Molecular Recognition, Vol. 18, Issue 2, p. 119-138 https://doi.org/10.1002/jmr.687	journal	January 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; 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
Modified Human Growth Hormone Cho, Ho Sung; Daniel, Thomas; Dimarchi, Richard https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20080102124 US Patent Application 11/923992; 20080102124	patent-application	May 2008
Binding Polypeptides and Uses Thereof Sidhu, Sachdev; Birtalan, Sara; Fellouse, Frederic https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20070202552 US Patent Application 11/566120; 20070202552	patent-application	August 2007
High-Level Expression of Tetanus Toxin Fragment C in Pichia Pastoris Strains Containing Multiple Tandem Integrations of the Gene Clare, J. J.; Rayment, F. B.; Ballantine, S. P. Nature Biotechnology, Vol. 9, Issue 5, p. 455-460 https://doi.org/10.1038/nbt0591-455	journal	May 1991
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
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
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
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
Production of carrier-peptide conjugates using chemically reactive unnatural amino acids Young, Travis; Schultz, Peter G. https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20100297693 US Patent Application 12/653274; 20100297693	patent-application	November 2010
In vivo incorporation of unnatural amino acids Schultz, Peter; Wang, Lei; Anderson, John Christopher https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/20030082575 US Patent Application 10/126927; 20030082575	patent-application	May 2003
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
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
Derivatization of non-natural amino acids and polypeptides Miao, Zhenwei; Liu, Junjie; Norman, Thea https://doi.org/https://image-ppubs.uspto.gov/dirsearch-public/print/downloadPdf/7385028 US Patent Document 7,385,028	patent	June 2008
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

Similar Records

Production of carrier-peptide conjugates using chemically reactive unnatural amino acids

Patent · Tue Dec 17 00:00:00 EST 2013 · OSTI ID:1210885

Young, Travis; Schultz, Peter G

Production of carrier-peptide conjugates using chemically reactive unnatural amino acids

Patent · Tue Jan 28 00:00:00 EST 2014 · OSTI ID:1210885

Young, Travis; Schultz, Peter G

In vivo unnatural amino acid expression in the methylotrophic yeast Pichia pastoris

Patent · Tue Aug 15 00:00:00 EDT 2017 · OSTI ID:1210885

Young, Travis; Schultz, Peter G.

Related Subjects

59 BASIC BIOLOGICAL SCIENCES

Title: Production of carrier-peptide conjugates using chemically reactive unnatural amino acids

Citation Formats

References (76)

Similar Records

Related Subjects