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

Young, Travis; Schultz, Peter G

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

Abstract

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.

Inventors:: Young, Travis; Schultz, Peter G

Issue Date:: 2014-01-28

Research Org.:: The Scripps Research Institute, La Jolla, CA, USA

Sponsoring Org.:: USDOE

OSTI Identifier:: 1117872

Patent Number(s):: 8637306

Application Number:: 12/653,274

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

Show more

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07K - PEPTIDES
C07K14/765 - Serum albumin, e.g. HSA
C07K14/78 - Connective tissue peptides, e.g. collagen, elastin, laminin, fibronectin, vitronectin, cold insoluble globulin [CIG]
C07K16/18 - against material from animals or humans
C07K19/00 - Hybrid peptides

C - CHEMISTRY C12 - BIOCHEMISTRY C12N - MICROORGANISMS OR ENZYMES
C12N15/62 - DNA sequences coding for fusion proteins
C12N15/815 - {for yeasts other than Saccharomyces}

C - CHEMISTRY C12 - BIOCHEMISTRY C12P - FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {
C12P21/02 - having a known sequence of two or more amino acids, e.g. glutathione

Show less

DOE Contract Number:: FG03-00ER46051

Resource Type:: Patent

Resource Relation:: Patent File Date: 2009 Dec 09

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

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                    Young, Travis, and Schultz, Peter G. Production of carrier-peptide conjugates using chemically reactive unnatural amino acids.  United States: N. p., 2014. 
        Web.

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                    Young, Travis, & Schultz, Peter G. Production of carrier-peptide conjugates using chemically reactive unnatural amino acids.  United States.

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                    Young, Travis, and Schultz, Peter G. Tue .  
        "Production of carrier-peptide conjugates using chemically reactive unnatural amino acids".  United States.  https://www.osti.gov/servlets/purl/1117872.

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@article{osti_1117872,

  title        = {Production of carrier-peptide conjugates using chemically reactive unnatural amino acids},

  author       = {Young, Travis and Schultz, Peter G},

  abstractNote = {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.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {2014},

  month        = {1}

}

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Patent:

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Proceedings of the National Academy of Sciences, Vol. 104, Issue 9, p. 3141-3146

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Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 1: Minimizing misacylation
journal, August 2007

Rodriguez, E. A.; Lester, H. A.; Dougherty, D. A.

RNA, Vol. 13, Issue 10

https://doi.org/10.1261/rna.666807

Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 2: Evaluating suppression efficiency
journal, August 2007

Rodriguez, E. A.; Lester, H. A.; Dougherty, D. A.

RNA, Vol. 13, Issue 10

https://doi.org/10.1261/rna.667607

tRNA genes and retroelements in the yeast genome
journal, February 1998

Hani, J.

Nucleic Acids Research, Vol. 26, Issue 3

https://doi.org/10.1093/nar/26.3.689

Development and Characterization of a Glucagon-Like Peptide 1-Albumin Conjugate: The Ability to Activate the Glucagon-Like Peptide 1 Receptor In Vivo
journal, March 2003

Kim, J. -G.; Baggio, L. L.; Bridon, D. P.

Diabetes, Vol. 52, Issue 3

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Unnatural Amino Acid Incorporation into Virus-Like Particles
journal, April 2008

Strable, Erica; Prasuhn, Duane E.; Udit, Andrew K.

Bioconjugate Chemistry, Vol. 19, Issue 4, p. 866-875

https://doi.org/10.1021/bc700390r

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

Patent 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.

Full Text Available

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

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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.

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Unnatural reactive amino acid genetic code additions

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This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, orthogonal pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

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Unnatural reactive amino acid genetic code additions

Patent Deiters, Alexander [La Jolla, CA]; Cropp, T Ashton [San Diego, CA]; Chin, Jason W [Cambridge, GB]; ...

This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNA synthetases, orthogonal pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

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Unnatural reactive amino acid genetic code additions

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This invention provides compositions and methods for producing translational components that expand the number of genetically encoded amino acids in eukaryotic cells. The components include orthogonal tRNAs, orthogonal aminoacyl-tRNAsyn-thetases, pairs of tRNAs/synthetases and unnatural amino acids. Proteins and methods of producing proteins with unnatural amino acids in eukaryotic cells are also provided.

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Similar Records

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

Abstract

Citation Formats

Glycoprotein synthesis patent, August 2005

In vivo incorporation of unnatural amino acids patent, May 2006

Methods and compositions for the production of orthogonal tRNA-aminoacyl tRNA synthetase pairs patent, August 2006

Glycoprotein synthesis patent, October 2006

Glycoprotein synthesis patent, February 2007

Glycoprotein synthesis patent, April 2007

Glycoprotein synthesis patent, May 2007

Glycoprotein synthesis patent, July 2007

Glycoprotein synthesis patent, August 2007

Derivatization of non-natural amino acids and polypeptides patent, June 2008

In vivo incorporation of unnatural amino acids patent-application, May 2003

patent-application, October 2004

Unnatural reactive amino acid genetic code additions patent-application, December 2004

Expanding the eukaryotic genetic code patent-application, January 2005

Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells patent-application, June 2005

Methods and composition for the production of orthogonal tRNA-aminoacyltRNA synthetase pairs patent-application, September 2005

Site-specific incorporation of redox active amino acids into proteins patent-application, October 2005

In vivo incorporation of unnatural amino acids patent-application, November 2005

Site specific incorporation of heavy atom-containing unnatural amino acids into proteins for structure determination patent-application, December 2005

Methods and composition for the production of orthogonal tRNA-aminoacyltRNA synthetase pairs patent-application, March 2006

In vivo incorporation of alkynyl amino acids into proteins in eubacteria patent-application, April 2006

Site-specific labeling of proteins for NMR studies patent-application, May 2006

In vivo site-specific incorporation of N-acetyl-galactosamine amino acids in eubacteria patent-application, May 2006

Adding photoregulated amino acids to the genetic code patent-application, June 2006

Compositions of orthogonal leucyl-trna and aminoacyl-trna synthetase pairs and uses thereof patent-application, July 2006

Compositions of orthogonal lysyl-tRNA and aminoacyl-tRNA synthetase pairs and uses thereof patent-application, August 2006

Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides patent-application, September 2006

Unnatural reactive amino acid genetic code additions patent-application, November 2006

Site-specific incorporation of redox active amino acids into proteins patent-application, January 2007

Composition of orthogonal glutamyl-trna and aminoacyl-trna synthetase pairs and uses thereof patent-application, January 2007

Compositions of orthogonal lysyl-trna and aminoacyl-trna synthetase pairs and uses thereof patent-application, February 2007

Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells patent-application, May 2007

In vivo incorporation of unnatural amino acids patent-application, May 2007

Expanding the eukaryotic genetic code patent-application, July 2007

Binding Polypeptides With Diversified And Consensus VH/VL Hypervariable Sequences patent-application, July 2007

Expanding the eukaryotic genetic code patent-application, July 2007

Glycoprotein synthesis patent-application, July 2007

Selective posttranslational modification of phage-displayed polypeptides patent-application, August 2007

Glycoprotein synthesis patent-application, August 2007

Binding Polypeptides and Uses Thereof patent-application, August 2007

Genetically programmed expression of proteins containing the unnatural amino acid phenylselenocysteine patent-application, October 2007

Systems for the expression of orthogonal translation components in eubacterial host cells patent-application, December 2007

Modified Human Growth Hormone patent-application, May 2008

Production of carrier-peptide conjugates using chemically reactive unnatural amino acids patent-application, November 2010

Addition of p-Azido-L-phenylalanine to the Genetic Code of Escherichia coli journal, July 2002

Incorporation of Nonnatural Amino Acids Into Proteins journal, June 2004

Albumin as a drug carrier: Design of prodrugs, drug conjugates and nanoparticles journal, December 2008

PEGylation, successful approach to drug delivery journal, November 2005

Yeast Systems for the Commercial Production of Heterologous Proteins journal, November 1991

Heterologous protein expression in the methylotrophic yeast Pichia pastoris journal, January 2000

Expression of Foreign Genes in the yeast Pichia pastoris book, January 2001

An Improved System for the Generation and Analysis of Mutant Proteins Containing Unnatural Amino Acids in Saccharomyces cerevisiae journal, August 2007

An Expanded Eukaryotic Genetic Code journal, August 2003

Operational strategies, monitoring and control of heterologous protein production in the methylotrophic yeast Pichia pastoris under different promoters: A review journal, April 2006

Adding Amino Acids with Novel Reactivity to the Genetic Code of Saccharomyces Cerevisiae journal, October 2003

Nucleophilic Catalysis of Oxime Ligation journal, November 2006

Control of protein phosphorylation with a genetically encoded photocaged amino acid journal, October 2007

Optimization of humanized IgGs in glycoengineered Pichia pastoris journal, January 2006

Detailed Analysis Concerning the Biodistribution and Metabolism of Human Calcitonin-Derived Cell-Penetrating Peptides journal, August 2008

Optimization of human serum albumin production in methylotrophic yeast Pichia pastoris by repeated fed-batch fermentation journal, January 2005

A strong nitrogen source-regulated promoter for controlled expression of foreign genes in the yeast Pichia pastoris journal, August 1998

High-level expression, purification, and characterization of recombinant human tumor necrosis factor synthesized in the methylotrophic yeast Pichia pastoris journal, May 1989

A genetically encoded fluorescent amino acid journal, June 2006

New Methods Enabling Efficient Incorporation of Unnatural Amino Acids in Yeast journal, May 2008

Addition of the keto functional group to the genetic code of Escherichia coli journal, December 2002

Adding amino acids to the genetic repertoire journal, December 2005

Expanding the Genetic Repertoire of the Methylotrophic Yeast Pichia pastoris journal, March 2009

Expression of heterologous proteins in Pichia pastoris: a useful experimental tool in protein engineering and production journal, January 2005

Pyrrolysine is not hardwired for cotranslational insertion at UAG codons journal, February 2007

Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 1: Minimizing misacylation journal, August 2007

Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 2: Evaluating suppression efficiency journal, August 2007

tRNA genes and retroelements in the yeast genome journal, February 1998

Development and Characterization of a Glucagon-Like Peptide 1-Albumin Conjugate: The Ability to Activate the Glucagon-Like Peptide 1 Receptor In Vivo journal, March 2003

Unnatural Amino Acid Incorporation into Virus-Like Particles journal, April 2008

Glycoprotein synthesis
patent, August 2005

In vivo incorporation of unnatural amino acids
patent, May 2006

Methods and compositions for the production of orthogonal tRNA-aminoacyl tRNA synthetase pairs
patent, August 2006

Glycoprotein synthesis
patent, October 2006

Glycoprotein synthesis
patent, February 2007

Glycoprotein synthesis
patent, April 2007

Glycoprotein synthesis
patent, May 2007

Glycoprotein synthesis
patent, July 2007

Glycoprotein synthesis
patent, August 2007

Derivatization of non-natural amino acids and polypeptides
patent, June 2008

In vivo incorporation of unnatural amino acids
patent-application, May 2003

Unnatural reactive amino acid genetic code additions
patent-application, December 2004

Expanding the eukaryotic genetic code
patent-application, January 2005

Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells
patent-application, June 2005

Methods and composition for the production of orthogonal tRNA-aminoacyltRNA synthetase pairs
patent-application, September 2005

Site-specific incorporation of redox active amino acids into proteins
patent-application, October 2005

In vivo incorporation of unnatural amino acids
patent-application, November 2005

Site specific incorporation of heavy atom-containing unnatural amino acids into proteins for structure determination
patent-application, December 2005

Methods and composition for the production of orthogonal tRNA-aminoacyltRNA synthetase pairs
patent-application, March 2006

In vivo incorporation of alkynyl amino acids into proteins in eubacteria
patent-application, April 2006

Site-specific labeling of proteins for NMR studies
patent-application, May 2006

In vivo site-specific incorporation of N-acetyl-galactosamine amino acids in eubacteria
patent-application, May 2006

Adding photoregulated amino acids to the genetic code
patent-application, June 2006

Compositions of orthogonal leucyl-trna and aminoacyl-trna synthetase pairs and uses thereof
patent-application, July 2006

Compositions of orthogonal lysyl-tRNA and aminoacyl-tRNA synthetase pairs and uses thereof
patent-application, August 2006

Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides
patent-application, September 2006

Unnatural reactive amino acid genetic code additions
patent-application, November 2006

Site-specific incorporation of redox active amino acids into proteins
patent-application, January 2007

Composition of orthogonal glutamyl-trna and aminoacyl-trna synthetase pairs and uses thereof
patent-application, January 2007

Compositions of orthogonal lysyl-trna and aminoacyl-trna synthetase pairs and uses thereof
patent-application, February 2007

Selective incorporation of 5-hydroxytryptophan into proteins in mammalian cells
patent-application, May 2007

In vivo incorporation of unnatural amino acids
patent-application, May 2007

Expanding the eukaryotic genetic code
patent-application, July 2007

Binding Polypeptides With Diversified And Consensus VH/VL Hypervariable Sequences
patent-application, July 2007

Expanding the eukaryotic genetic code
patent-application, July 2007

Glycoprotein synthesis
patent-application, July 2007

Selective posttranslational modification of phage-displayed polypeptides
patent-application, August 2007

Glycoprotein synthesis
patent-application, August 2007

Binding Polypeptides and Uses Thereof
patent-application, August 2007

Genetically programmed expression of proteins containing the unnatural amino acid phenylselenocysteine
patent-application, October 2007

Systems for the expression of orthogonal translation components in eubacterial host cells
patent-application, December 2007

Modified Human Growth Hormone
patent-application, May 2008

Production of carrier-peptide conjugates using chemically reactive unnatural amino acids
patent-application, November 2010

Addition of p-Azido-L-phenylalanine to the Genetic Code of Escherichia coli
journal, July 2002

Incorporation of Nonnatural Amino Acids Into Proteins
journal, June 2004

Albumin as a drug carrier: Design of prodrugs, drug conjugates and nanoparticles
journal, December 2008

PEGylation, successful approach to drug delivery
journal, November 2005

Yeast Systems for the Commercial Production of Heterologous Proteins
journal, November 1991

Heterologous protein expression in the methylotrophic yeast Pichia pastoris
journal, January 2000

Expression of Foreign Genes in the yeast Pichia pastoris
book, January 2001

An Improved System for the Generation and Analysis of Mutant Proteins Containing Unnatural Amino Acids in Saccharomyces cerevisiae
journal, August 2007

An Expanded Eukaryotic Genetic Code
journal, August 2003

Operational strategies, monitoring and control of heterologous protein production in the methylotrophic yeast Pichia pastoris under different promoters: A review
journal, April 2006

Adding Amino Acids with Novel Reactivity to the Genetic Code of Saccharomyces Cerevisiae
journal, October 2003

Nucleophilic Catalysis of Oxime Ligation
journal, November 2006

Control of protein phosphorylation with a genetically encoded photocaged amino acid
journal, October 2007

Optimization of humanized IgGs in glycoengineered Pichia pastoris
journal, January 2006

Detailed Analysis Concerning the Biodistribution and Metabolism of Human Calcitonin-Derived Cell-Penetrating Peptides
journal, August 2008

Optimization of human serum albumin production in methylotrophic yeast Pichia pastoris by repeated fed-batch fermentation
journal, January 2005

A strong nitrogen source-regulated promoter for controlled expression of foreign genes in the yeast Pichia pastoris
journal, August 1998

High-level expression, purification, and characterization of recombinant human tumor necrosis factor synthesized in the methylotrophic yeast Pichia pastoris
journal, May 1989

A genetically encoded fluorescent amino acid
journal, June 2006

New Methods Enabling Efficient Incorporation of Unnatural Amino Acids in Yeast
journal, May 2008

Addition of the keto functional group to the genetic code of Escherichia coli
journal, December 2002

Adding amino acids to the genetic repertoire
journal, December 2005

Expanding the Genetic Repertoire of the Methylotrophic Yeast Pichia pastoris
journal, March 2009

Expression of heterologous proteins in Pichia pastoris: a useful experimental tool in protein engineering and production
journal, January 2005

Pyrrolysine is not hardwired for cotranslational insertion at UAG codons
journal, February 2007

Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 1: Minimizing misacylation
journal, August 2007

Improved amber and opal suppressor tRNAs for incorporation of unnatural amino acids in vivo. Part 2: Evaluating suppression efficiency
journal, August 2007

tRNA genes and retroelements in the yeast genome
journal, February 1998

Development and Characterization of a Glucagon-Like Peptide 1-Albumin Conjugate: The Ability to Activate the Glucagon-Like Peptide 1 Receptor In Vivo
journal, March 2003

Unnatural Amino Acid Incorporation into Virus-Like Particles
journal, April 2008