Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides
Reexamination Certificate
2006-04-18
2006-04-18
Campell, Bruce R. (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Synthesis of peptides
C530S326000, C530S333000, C530S339000, C530S350000, C530S402000, C435S283100
Reexamination Certificate
active
07030217
ABSTRACT:
The present invention provides methods, apparatus and kits for synthesizing assembled peptides and proteins on a solid phase with sequential ligation of three or more unprotected peptide segments using chemoselective and mild ligation chemistries in aqueous solution. Also provided are methods of monitoring solid phase sequential ligation reactions using MALDI or electrospray ionization mass spectrometry of reaction products.
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patent: 6329468 (2001-12-01), Wang
patent: WO 96/34878 (1996-11-01), None
patent: WO 98/28434 (1998-07-01), None
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Canne et al., “Synthesis Of Versatile Purification Handle For Use With Boc Chemistry Solid Phase Peptide Synthesis,”Tetrahedron Letters, 38(19):3361-3364 (1997).
Cheng et al., “Chemical Synthesis Of Human β-Endorphin(1-27) Analogs By Peptide Segment Coupling,”Int. J. Pept. Prot. Res., 38:70-78 (1991).
Dawson et al., “Synthesis Of Proteins By Native Chemical Ligation,”Science, 266:776-779 (1994).
Funakoshi et al., “Chemoselective one-step purification method for peptides synthesized by the solid-phase technique,”Proc. Natl. Acad. Sci. USA, 88:6981-6985 (1991).
Funakoshi et al., “Affinity Purification Method For Using Reversible Biotinylating Reagent For Peptides Synthesized By The Solid-Phase Technique,”J. Chromatog., 638:21-27 (1995).
Garcia-Echeverria et al., “One The Use Of Hydrophobic Probes In The Chromatographic Purification Of Solid-Phase-Synthesized Peptides,”J. Chem. Soc., Chem Commun., 779-780 (1995).
Hojo et al., “Polypeptide Synthesis Using The S-Alkyl Thioester Of A Partially Protected Segment. Synthesis Of The DNA-Binding Doman Of c-Myb Protein (142-193)-NH2,”Bull. Chem. Soc. Jpn., 64:111-117 (1991).
Hojo et al., “Protein Synthesis Using S-Alkyl Thioester Of Partially Protected Peptide Segments, Synthesis Of DNA-Binding Domain Of c-Myb Protein (142-193)-NH2,”Bull. Chem. Soc. Jpn., 65:3055-3063 (1992).
Liu et al., “Peptide Segment Ligation Strategy Without Use Of Protecting Groups,”Proc. Natl. Acad. Sci. USA, 91:6584-6588 (1994).
M. Janssen, “Thiolo, Thiono, And Dithio Acids And Esters,” Chapter 15 of The Chemistry of Carboxylic Acids and Their Esters (1969).
Muramatsu et al., “Localization Of Heparin-Binding, Neurite Outgrowth And Antigenic Regions In Midkine Molecule,”Biochem. And Biophys. Res. Comm., 203(2):1131-1139 (1994).
Rose et al., “Facile Synthesis Of Homogeneous Artificial Proteins,”J. Am. Chem. Soc., 116:30-34 (1994).
Schnolzer et al., “Constructing Proteins By Dovetailing Unprotected Synthetic Peptides: Backbone-Engineered HIV Protease,”Science, 256:221-225 (1992).
Tam et al., “Peptide Synthesis Using Unprotected Peptides Through Orthogonal Coupling Methods,”Proc. Natl. Acad. Sci. USA, 92:12485-12489 (1995).
Akaji et al., “Studies On Peptides. CXXVII. Synthesis Of A Tripentacontapeptide With Epidermal Growth Factor Activity,”Chem. Pharm. Bull. (Tokyo) 33:184-102 (1985).
Atherton et al., “Solid Phase Fragment Condensation—The Problems,” In Innovation And Perspective In Solid Phase Synthesis, R. Epton et al. Eds., pp. 11-25 (1990).
Aimoto, “Synthesis of Phosphorylated Calmodulin-binding Site of Ca2+/Calmodulin-dependent Protein Kinase IICAMII by a Thioester Method,”Chemical Abstracts, vol. 125, No. 1, Abstract No. 11415, (1996).
Akaji, et al., “Stiudies On Peptides. CXXVII. Synthesis Of A Tripentacontapeptide With Epidermal Growth Factor Activity,”Chem. Pharma. Bull. (Tokyo) 33:184-102 (1985).
Atherton, et al., “Solid Phase Fragment Condensation—The Problems,”In Innovation and Perspective In Solid Phase Synthesis, R. Epton, et al. Eds., pp. 11-25 (1990).
Ball, et al., “Affinity Purification Of 101 Residue Rat Cpn 10 Using A Reversibe Biotinylated Probe,”J. Pept. Sci., 1:288-294 (1995).
Canne, et al., “Synthesis Of Versatile Purification Handle For Use With Boc Chemistry Solid Phase Peptide Synthesis,”Tetrahedron Letters, 38(19):3361-3364 (1997).
Canne, “Extending the Applicability of Native Chemical Ligation,”J. Am. Che. Soc., vol. 118:5891-5896 (1996).
Canne, “A General Method For The Synthesis Of Thioester Resin Linkers For Use In The Solid Phase Synthesis Of Peptide-α-Thioacids,”Tetrahedron Letters, 36(8):1217-1220 (1995).
Cheng, et al., “Chemical Synthesis Of Human β-Endorphin(1-27) Analogs By Peptide Segment Coupling,”Int. J. Pept. Prot. Res., 38:70-78 (1991).
Dawson, et al., “Synthesis Of Proteins By Native Chemical Ligation,”Science, 266:766-799 (1994).
Funakoshi, et al., “Chemoselective One-Step Purification Method For Peptides Synthesized by the Solid Phase Technique,” Proc. Natl. Acad. Sci. USA, 88:6981-6985 (1991).
Funakoshi, et al., “Affinity Purification Method Using Reversible Biotinylating Reagent For Peptides Synthesized By The Solid-Phase Technique,”J. Chromatog., 638:21-27 (1995).
Garcia-Echeverria, et al., “One The Use of Hydrophobic Probes In The Chromatographic Purification Of Solid-Phase-Synthesized Peptides,”J. Chem. Soc. Chem. Commun., 779-780 (1995).
Hojo, “Development of a Linker With an Enhanced Stability for the Preparation of Peptide Thioesters and Its Application to the Synthesis of a Stable-Isotope-Labelled HU-Type DNA-Binding Protein,”Bull. Chem. Soc. Japan, 66(9):2700-2706 (1993).
Hojo, et al., “Protein Synthesis Using S-Alkyl Thioester Of Partially Protected Peptide Segments, Synthesis of DNA-Binding Domain Of c-Myb Protein (142-193)-NH2,”Bull. Chem. Soc. Japan, 65:3055-3063 (1992).
Hojo, et al., “Polypeptide Synthesis Using the S-Alkyl Thioester of a Partially Protected Segment: Synthesis of the DNA-Binding Domain of c-Myb Protein (142-193)-NH2,”Bull. Chem. Soc. Japan, 64:111-117 (1991).
Janssen, “Thiolo, Thiono, and Dithio Acids and Ester,” Chapter 15,The Chemistry of Carboxylic Acids and Esters(1969).
Liu, et al., “Peptide Segment Ligation Strategy Without Use Of Protecting Groups,”Proc. Natl. Acad. Sci. USA, 91:6584-6588 (1994).
Muramatsu, et al., “Localization of Heparin-Binding, Neurite Outgrowth and Antigenic Regions In Midkine Molecule,”Biochem. And Biophys. Res. Comm., 203(2):1131-1139 (1994).
Rose, et al., “Facile Synthesis Of Homogeneous Artificial Proteins,”J. Am. Chem. Soc., 116:30-34 (1994).
Schnolzer, et al., “Constructing Proteins By Dovetailing Unprotected Synthetic Peptides: Backbone-Engineered HIV Protease,”Science, 256:221-225 (1992).
Tam, et al., “Peptide Synthesis Using Unprotected Peptides Through Orthogonal Coupling Methods,”Proc. Natl. Acad. Sci. USA, 92:12485-12489 (1995).
Canne Lynne
Kent Stephen B. H.
Simon Reyna
Auerbach Jeffery
Campell Bruce R.
Gryphon Therapeutics, Inc.
Gupta Anish
Joyce Catherine
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