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
Russel, Jeffrey Edwin (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Synthesis of peptides
C530S300000, C530S345000, C530S350000, C530S351000, C530S399000
Reexamination Certificate
active
07030218
ABSTRACT:
The present invention concerns methods and compositions for extending the technique of native chemical ligation of a wider range of peptides, polypeptides, other polymers and other molecules via an amide bond (see FIG.1). The invention further provides methods and uses for such proteins and derivatized proteins. The invention is particularly suitable for use in the synthesis of optionally polymer-modified, synthetic bioactive proteins, and of pharmaceutical compositions that contain such proteins.
REFERENCES:
patent: 3853832 (1974-12-01), Li
patent: 4565785 (1986-01-01), Gilbert et al.
patent: 4659558 (1987-04-01), Urquhart et al.
patent: 4673641 (1987-06-01), George et al.
patent: 4710473 (1987-12-01), Morris
patent: 4738921 (1988-04-01), Belagaje et al.
patent: 4795706 (1989-01-01), Hsiung et al.
patent: 4810499 (1989-03-01), Nuwayser
patent: 5079230 (1992-01-01), Randawa et al.
patent: 5438040 (1995-08-01), Ekwuribe
patent: 5589356 (1996-12-01), Tam
patent: 5641511 (1997-06-01), Kuhrts
patent: 5646285 (1997-07-01), Baindur et al.
patent: 5654000 (1997-08-01), Poli et al.
patent: 5681811 (1997-10-01), Ekwuribe
patent: 5690954 (1997-11-01), Illum
patent: 5756672 (1998-05-01), Builder et al.
patent: 5759566 (1998-06-01), Poli et al.
patent: 5766633 (1998-06-01), Milstein et al.
patent: 5783212 (1998-07-01), Fassihi et al.
patent: 5792451 (1998-08-01), Sarubbi et al.
patent: 5849331 (1998-12-01), Ducheyne et al.
patent: 5854389 (1998-12-01), Kent et al.
patent: 5879712 (1999-03-01), Bomberger et al.
patent: 6002961 (1999-12-01), Mitragotri et al.
patent: 6013283 (2000-01-01), Greenwald et al.
patent: 6017318 (2000-01-01), Gauthier et al.
patent: 6018678 (2000-01-01), Mitragotri et al.
patent: 6027720 (2000-02-01), Kuga et al.
patent: 6041253 (2000-03-01), Kost et al.
patent: 6072041 (2000-06-01), Davis et al.
patent: 6410708 (2002-06-01), Ashkenazi et al.
patent: 6552167 (2003-04-01), Rose
patent: 6635257 (2003-10-01), Depla et al.
patent: 0 459 630 (1991-04-01), None
patent: WO 91/19735 (1991-12-01), None
patent: WO 95/00846 (1995-01-01), None
patent: WO 96/17935 (1996-06-01), None
patent: WO 96/34878 (1996-11-01), None
patent: WO 97/44054 (1997-11-01), None
patent: WO 98/28434 (1998-07-01), None
patent: WO 99/11655 (1999-03-01), None
patent: WO 99/11666 (1999-03-01), None
patent: WO 02/04015 (2002-01-01), None
patent: WO 02/20034 (2002-03-01), None
Gloss et al. Examining the Structural and Chemical Flexibility . . . Biochemistry. vol. 34, pp. 12323-12332 (1995).
Or et al. Cysteine Alkylation in Unprotected Peptides . . . Journal of Organic Chemistry. vol. 56, pp. 3146-3149 (1991).
Crow et al. Inhibition Of Early Hematopoietic Progenitors . . . Blood. Nov. 15, 1994. vol. 84, No. 10, Supplement 1, p. 127a, Abstract No. 492.
Ahuja, Satinder, ‘Chiral separations and technology: an overview.’Chiral Sep.(1997), 1-7.
Ahuja, Satinder. ‘Chiral separations. An overview.’ACS Symp. Ser.(1991), 471 Chiral Sep. Liq. Chromatogr.
Yajima, H. et al., “Solution synthesis of a tetratetracontapeptide amide with growth hormone releasing activity,”Chem Pharm Bull(Tokyo) (1983) May;31(5):1800-2.
Akira S, et al: “Interleukin-6 in biology and medicine,”Adv Immunol(1993) 54:1-78.
Atherton E., et al., “Solid Phase Fragment Condensation—The Problems,”Innovation and Perspectives in Solid Phase Synthesis11-25, not dated.
Baca, M. et al., “Chemical Ligation of Cysteine-Containing Peptides: Synthesis of a 22 kDa Tethered Demer of HIV-1 Protease,”J. Amer. Chem Soc.(1995) 117:1881-1887.
Baggiolini M, et al., “Human chemokines: an update,”Am. Rev. Immunol(1997) 15:675-705.
Botti, P. et al., “Native Chemical Ligation Using Removable N.alpha -(1-phenyl-2-mercaptoethyl) Auxiliaries,”Tetrahedron Letters42, 1831-1833 (2001).
Brems et al., “Equilibrium denaturation of pituitary- and recombinant-derived bovine growth hormone”Biochemistry1985 Dec. 17;24(26):7662-8.
Canne et al., “A General Method for the Synthesis of Thioester Resin Linkers for Use in the Solid Phase Synthesis of Peptide-alpha-Thioacids,”Tetrahedron Lett.(1995) 36:1217-1220.
Canne L.E. et al., “Solid Phase Protein Synthesis by Chemical Ligation of Unprotected Peptide Segments in Aqueous Solution,”Peptides: Frontiers of Peptide Science, Proceedings of the American Peptide Symposium,15th, Nashville, Tennessee, Jun. 14-19, 1997, 301-302 (1999).
Canne L.E. et al., “The Total Chemical Synthesis of L- and D-superoxide Dismutase,”Protein Engineering,10-23 (1997).
Chan, T.-H. et al., “Synthesis of Phosphonic Acid Analogues of Sialic Acids (Neu5Ac and KDN) as Potential Sialidase Inhibitors,”J. Org. Chem.(1997) 62:3500-3504.
Chen GH, et al, “Effect of granulocyte-macrophage colony-stimulating factor on rat alveolar macrophage anticryptococcal activity in vitro,”J Immunol1994 Jan. 15;152(2):724-34.
Chong et al., “Single-column purification of free recombinant proteins using a self-cleavable affinity tag derived from a protein splicing element,”Gene1997 Jun. 19;192(2):271-281.
Chong et al., “Utilizing the C-terminal cleavage activity of a protein splicing element to purify recombinant proteins in a single chromatographic step,”Nucleic Acids Res.1998 Nov. 15;26(22):5109-5115.
Collet, Andre. “Separation Purification of Enantiomers by Crystallization Methods”,Enantiomer(1999) 4:157-172.
Cotton et al., “Peptide Ligation and Its application to protein engineering,”Chemistry&Biology(1999) 6(9):247-256.
Dawson et al., “Synthesis of Chemokines by Native Chemical Ligation,”Methods Enzymol.(1997)287:34-45.
Dawson et al., “Synthesis of Native Proteins By Chemical Ligation,”Ann. Rev. Biochem(2000) 69:923-960.
Dawson, P.E. et al. Synthesis of Proteins by Native Chemical Ligation, Science 266, 776-779 (1994).
Dordal, M.S. et al. “The role of carbohydrate in erythropoietin action,” (1985)Endocrinology116:2293.
Englebretsen, et al., “A Novel Thioether Linker: Chemical Synthesis of a HIV-1 Protease Analogue by Thioether Ligation,”Tet. Letts.(1995) 36(48):8871-8874.
Evans et al., “Semisynthesis of cytotoxic proteins using a modified protein splicing element,”Protein Science(1998) 7:2256-2264.
Gaertner et al., “Site Specific Attachment of Functionalized Poly(ethylene glycol) to the Amino Terminus of Proteins,”Bioconjug. Chem.(1996) 7(1):38-44.
Gaertner H.F.G., et al., “Chemical Ligation of Proteins and Other Macromolecules, Peptides: Chemistry, Structure and Biology,”Proceedings of the American Peptide Symposium,14th, Columbus, Ohio, Jun. 18-23, 1995, 18-20 (1996).
Gaertner, et al., “Site-specific religation of G-CSF fragments through a thioether bond,”Bioconjug Chem.1994 Jul.-Aug.;5(4):333-338.
Gieselman et al., “Synthesis of a selenocysteine-containing peptide by native chemical ligation,”Org Lett.May 3, 2001;3(9):1331-1334.
Goldwasser, E. et al. “On the mechanism of erythropoietin-induced differentiation. 13. The role of sialic acid in erythropoietin action,”J Biol Chem.Jul. 10, 1974;249(13):4202-6.
Goodson et al. “Site-Directed Pegylation Of Recombinant Interleukin-2 At Its Glycosylation Site,”BiotechnologyApr. 1990, vol. 8, pp. 343-346.
Hackeng et al., “Protein synthesis by native chemical ligation: expanded scope by using straightforward methodology,”Proc Natl Acad Sci U S A.Aug. 31, 1999;96(18):10068-73.
Higuchi, M. et al, “Role of Sugar Chains in the Expression of the Biological Activity of Human Erythropoietin,” (1992)J. Biol. Chem.267:7703-7709.
Hojo H, et al., “Polypeptide Synthesis Using the S-Alkyl Thioester of a Partially Protected Peptide Segment. Synthesis of the DNA-Binding Domain ofc-Myb Protein (142-193)-NH2” (1991)Bull Chem Soc Jpn 64:111-117.
Howard M, et al, “Biological Properties of Interleukin 10,
Botti Paolo
Bradburne James A.
Chen Shiah-yun
Cressman Sonya
Hunter Christie L.
Auerbach Jeffrey I.
Berenato White & Stavish LLC
Gryphon Therapeutics
Russel Jeffrey Edwin
LandOfFree
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