Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides
Reexamination Certificate
2009-08-28
2011-11-15
Cordero Garcia, Marcela M (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Synthesis of peptides
C530S335000, C530S336000, C530S337000
Reexamination Certificate
active
08058393
ABSTRACT:
An instrument and method for accelerating the solid phase synthesis of peptides are disclosed. The method includes the steps of deprotecting a protected first amino acid linked to a solid phase resin by admixing the protected linked acid with a deprotecting solution in a microwave transparent vessel while irradiating the admixed acid and solution with microwaves, activating a second amino acid, coupling the second amino acid to the first acid while irradiating the composition in the same vessel with microwaves, and cleaving the linked peptide from the solid phase resin by admixing the linked peptide with a cleaving composition in the same vessel while irradiating the composition with microwaves.
REFERENCES:
patent: 3531258 (1970-09-01), Merrifield et al.
patent: 3581190 (1971-05-01), Brown
patent: 3647390 (1972-03-01), Kubodera et al.
patent: 3926556 (1975-12-01), Boucher
patent: 4192798 (1980-03-01), Fuller et al.
patent: 4696981 (1987-09-01), Harada et al.
patent: 4746490 (1988-05-01), Saneii
patent: 5288464 (1994-02-01), Nokihara
patent: 5380495 (1995-01-01), Chang et al.
patent: 5382414 (1995-01-01), Lautenschlager
patent: 5387397 (1995-02-01), Strauss et al.
patent: 5830417 (1998-11-01), Kingston
patent: 5932075 (1999-08-01), Strauss et al.
patent: 6028172 (2000-02-01), Stepaniuk et al.
patent: 6034361 (2000-03-01), Hudak
patent: 6171555 (2001-01-01), Cargill et al.
patent: 6288379 (2001-09-01), Greene et al.
patent: 6320025 (2001-11-01), Slavazza et al.
patent: 6326090 (2001-12-01), Schultz et al.
patent: 6486455 (2002-11-01), Merabet
patent: 6630652 (2003-10-01), Jennings
patent: 6713719 (2004-03-01), De Steur et al.
patent: 6744024 (2004-06-01), Hayes et al.
patent: 6858434 (2005-02-01), Williams
patent: 6867400 (2005-03-01), Collins et al.
patent: 6917023 (2005-07-01), Hayes et al.
patent: 7393920 (2008-07-01), Collins et al.
patent: 2002/0117498 (2002-08-01), Jennings
patent: 2003/0082633 (2003-05-01), Martin et al.
patent: 2003/0089706 (2003-05-01), Jennings
patent: 2003/0199099 (2003-10-01), King et al.
patent: 2004/0020923 (2004-02-01), Collins et al.
patent: 2006/0025567 (2006-02-01), Collins et al.
patent: 2006/0025568 (2006-02-01), Collins et al.
patent: 2006/0025569 (2006-02-01), Collins et al.
patent: 2007/0090104 (2007-04-01), Collins et al.
patent: 2007/0270573 (2007-11-01), Collins
patent: 2009/0012264 (2009-01-01), Collins et al.
patent: 2009/0221792 (2009-09-01), Collins et al.
patent: 2010/0048865 (2010-02-01), Collins et al.
patent: 0 541 340 (1993-05-01), None
patent: 1 491 552 (2004-12-01), None
patent: 1 533 025 (2005-05-01), None
patent: 2004/002617 (2004-01-01), None
European Search Report of foreign counterpart application No. EP05101287.0; mailed Nov. 21, 2007; 3 pages.
Ferguson, “Focused microwave instrumentation from CEM Corporation,” Molecular Diversity 2003, vol. 7, Nr. 2-4, pp. 281-286.
Park, et al., “New Reaction Vessel for Solid-Phase Peptide Synthesis,” Canadian Journal of Biochemistry, National Research Council of Canada, Ottawa, vol. 50, No. 7, Jan. 1972, pp. 755-757.
Caddick, “Microwave Assisted Organic Reactions,” Tetrahedron 1985, United Kingdom, vol. 51, No. 38, 1995; pp. 10403-10432.
Kramer et al, “Synthesis and Screening of Peptide Libraries on Continuous Cellulose Membrane Supports”, Methods in Molecular Biology, vol. 87: Combinatorial Peptide Library Protocols; Humana Press, Inc.; Totowa, NJ; pp. 25-39, Dec. 1997.
Hilpert et al., “Anti-c-myc antibody 9E10: epitope key positions and variability characterized using peptide spot synthesis on cellulose,” Protein Engineering, Oct. 2001, vol. 14, No. 10, pp. 803-806.
Frank, “The Spot-synthesis technique. Synthetic peptide arrays on membrane supports-principles and applications,” 2002, Journal of Immunological Methods. vol. 267, pp. 13-26.
Overview of Peptide Synthesis. Anaspec. Accessed online Feb. 15, 2006 at http:/www.anaspec.com/html/peptide—notes. html, pp. 1-11.
Kappe, “Speeding Up Solid-Phase Chemistry by Microwave Irradiation. A Tool for High-Throughout Synthesis,” American Laboratory, 2001, vol. 33, No. 10, pp. 13-16 and 18-19.
Murray et al.,“Efficient Synthesis of a B-Peptide Combinatorial Library with Microwave Irradiation,” JACS. 2005, vol. 127, pp. 13271-13280.
Al-Obeidi et al., “Microwave-Assisted Solid-phase Synthesis (MASS): Parallel and Combinatorial Chemical Library Synthesis,” Mini Reviews in Medicinal Chemistry. 2003, vol. 3, pp. 449-460.
Lew et al., “Increasing Rates of Reaction: Microwave-Assisted Organic Synthesis for Combinatorial Chemistry,” J Comb Chem. Mar./Apr. 2002. vol. 4, No. 2, pp. 95-105.
Lange et al., “Recent Advances in Microwave-Assisted Combinatorial Synthesis and Library Generation,” Combinational Chemistry and High Throughput Screening. 2005, vol. 8, pp. 595-606.
Scharn et al., “Spatially Addressed Synthesis of Amino-and Amino-Oxy-Substituted 1,3,5-Triazine Arrays on Polymeric Membranes,” J Comb Chem. 2000, vol. 2, pp. 361-369.
Scharn et al., “Sequential Nucleophilic Substitution on Halogenated Triazines, Pyrimidines, and Purines: A Novel Approach to Cyclic Peptidomimetics,” J Org Chem. 2001, vol. 66, pp. 507-513.
Wang et al., Enhancement of Coupling Reaction in Peptide Synthesis by Microwave Irradiation, 12 pages. 1990, 1992 and 1997.
Merrifield, “Concept and early development of solid-phase peptide synthesis,” Methods Enzymol. 1997; 289: 3-13.
Albericio et al., “Coupling Reagents and Activation,” Methods Enzymol. 1997; 289: 104-126.
Erdelyi et al., “Rapid Microwave-assisted Solid Phase Peptide Synthesis,” Synthesis 2002 Germany, No. 11, 2002 Germany, No. 11, 2002, pp. 1592-1596.
Yu et al., “Enhanced Coupling Efficiency in Solid-Phase Peptide Synthesis by Microwave Irradiation,” Journal of Organic Chemistry, vol. 57, No. 18, 1992, pp. 4781-4784.
Santagada, et al. “Microwave-Enhanced Solution Coupling of the Alpha, Alpha-dialkyl Amino Acid, Aib, ”Tetrahedron Letters, vol. 42, No. 31, Jul. 30, 2001, pp. 5171-5173.
Daga, et al., “Rapid Microwave-Assisted Deprotection of N-Cbz and N-Bn Derivatives,” Tetrahedron Letters, Jul. 30, 2001 United Kingdom, vol. 42, No. 31, pp. 5191-5194.
Collins, et al., “Novel Method for Enhanced Solid Phase Peptide Synthesis Using Microwave Energy,” Biopolymers, vol. 71, No. 3, 2003, p. 361.
Porcheddu et al., “A New, Rapid, General Procedure for the Synthesis of Organic Molecules Supported on Methoxy-Polyethylene Glycol (MeOPEG) under Microwave Irradiation Conditions,” Eur. J. Org. Chem. 2003, pp. 907-912.
Kramer et al., “Combinatorial Cellulose-Bound Peptide Libraries: Screening Tools for the Identification of Peptides that bind Ligands with Predefined Specificity,” Methods: A companion to Methods in Enzymology. 1994, vol. 6, pp. 388-395.
Stadler et al., “High-Speed Couplings and Cleavages in Microwave-Heated, Solid-Phase Reactions at High Temperatures,” Eur. J. Org. Chem. 2001. pp. 919-925.
Yu et al., “Enhanced Coupling Efficiency in Solid-Phase Peptide Synthesis by Microwave Irradiation,” The Journal of Organic Chemistry, Aug. 28, 1992, pp. 4781-4785, vol. 57, No. 18, American Chemical Society 1992.
Erdelyi et al., “Rapid Microwave-Assisted Solid Phase Peptide Synthesis,” Synthesis 2002, Aug. 22, 2002, pp. 1592-1596, No. 11.
Chen et al., “The Studies of Microwave Effects on the Chemical Reactions,” Journal of the Chinese Chemical Society, 1997, pp. 169-182, vol. 44, No. 3.
Chen et al., “Enhancement of Chemical Reactions by Microwave Irradiation,” Journal of the Chinese Chemical Society, 1991, pp. 85-91, vol. 38. No. 1; Only 1 page Abstract enclosed.
Olivos et al., Microwave-Assisted Solid-Phase Synthesis of Peptoids, Organic Letters, 2002, pp. 4057-4059, vol. 4, No. 23, 2002 American Chemical Society.
Rao et al., Microwave Assisted High Yi
Collins Jonathan McKinnon
Collins Michael John
Lambert Joseph Joshua
CEM Corporation
Cordero Garcia Marcela M
Summa, Additon & Ashe, P.A.
LandOfFree
Microwave-assisted peptide synthesis does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Microwave-assisted peptide synthesis, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Microwave-assisted peptide synthesis will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4284843