Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides
Patent
1996-12-05
1999-01-12
Green, Lora M.
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Synthesis of peptides
530333, 530334, 530335, 436501, 436518, 435 71, C07K 108, G01N 33566, G01N 33543, G01N 3353
Patent
active
058591915
ABSTRACT:
A peptide comprising a free terminal alpha amine is treated with an aryl sulfonamide activating agent, resulting in an activated amide. The resulting activated amide is deprotonated with a base and modified by the addition of a substituent group. The aryl sulfonamide activating group is cleaved using a nucleophilic substitution reaction. The method is particularly useful for the modification of peptides at specific N-alpha positions, and is compatible with conventional solid phase peptide synthesis, including those that utilize Fmoc protecting groups.
REFERENCES:
patent: 4108846 (1978-08-01), Meienhofer
patent: 4219497 (1980-08-01), Plattner et al.
patent: 5010175 (1991-04-01), Rutter et al.
patent: 5182366 (1993-01-01), Huebner et al.
patent: 5225533 (1993-07-01), Rutter et al.
patent: 5266684 (1993-11-01), Rutter et al.
patent: 5420246 (1995-05-01), Rutter et al.
patent: 5438119 (1995-08-01), Rutter et al.
patent: 5463564 (1995-10-01), Agrafiotis et al.
patent: 5545568 (1996-08-01), Ellman
patent: 5556762 (1996-09-01), Pinilla et al.
patent: 5565324 (1996-10-01), Still et al.
patent: 5573905 (1996-11-01), Lerner et al.
Fukuyama et al. 2,4-dinitrobenzenesulfonamides: A Simple and Practical Method for the Preparation of a Variety of Secondary Amines and Diamines. Tetrahedron Letters, vol. 38(33):5831-5834, 1997.
Handbook of Chemistry and Physics, 61st edition, 1980-1981, CRC Press Boca Raton Florida see pp. D-167, 1981.
Zwierzak, A and Podstawczynska, I., Phase-Transfer Catalyzed Alkylation of Diphenylphosphinic amide--A New Versatile Synthesis of Primary and Secondary Amines. Angew. Chem. Int. Ed. Engl. vol. 16, No. 10. pp. 702-704, 1977.
Advanced Organic Chemistry, Part B: Reactions and synthesis 3ird edition. Francis A. Carey and Richard J. Sundberg. Plenum Press, New York, 1990.
Advanced Organic Chemistry, 4 edition. Jerry March. John Wiley and Sons, New York, 1992.
Ali, F., et al., 1994, "Conformationally constrained peptides and semipeptides derived from RGD as potent inhibitors of the platelet fibrinogen receptor and platelet aggregation," J. Med. Chem. 37:769-80.
Blake, J., et al., "Use of combinatorial peptide libraries to construct functional mimics of tumor epitopes recognized by MHC class I-restricted cytolytic T lymphocytes," 1996, J. Exp. Med. 184:121-30.
Blondelle, S.E., et al., 1996, "Rapid identification of compounds with enhanced antimicrobial activity by using conformationally defined combinatorial libraries," Biochem. J. 313:141-7.
Fukuyama, T., et al., 1995, "2-and 4-nitrobenzenesulfonamides: Exceptionally versatile means for preparation of secondary amines and protection of amines," Tetrahedron Let. 36(36):6373-6374.
Han, H., et al., 1995, "Liquid-phase combinatorial synthesis," Proc. Natl. Acad. Sci. USA 92(14):6419-23.
Kaljuste, K., and Unden, A., 1993, "New method for the synthesis of N-methyl amino acids containing peptides by reductive methylation of amino groups on the solid phase," Int. J. Peptide Protein Res. 42:118-124.
Krchnak, V., et al., 1995, "Linear presentation of variable side-chain spacing in a highly diverse combinatorial library," Peptide Research 8(4):198-205.
McBride, J.D., et al., 1996, "Selection of chymotrypsin inhibitors from a conformationally-constrained combinatorial peptide library," J. Mol. Biol. 259:819-27.
Merrifield, R.B., 1969, "Solid-phase peptide synthesis," Advances in Enzymology 32:221-296.
Ostresh, et al., 1994, "Libraries from libraries: Chemical transformation of combinatorial libraries to extend the range and repertoire of chemical diversity," Proc. Natl. Acad. Sci. USA 91:11138-42.
Perez-Paya, E., et al., 1996, "Functionalized protein-like structures from conformationally defined synthetic combinatorial libraries," J. Biol. Chem. 271:4120-6.
Rizo, J., and Gierasch, L.M., 1992, "Constrained peptides: Models of bioactive peptides and protein substructures," Ann. Rev. Biochem. 61:387-418.
Schmidt, R., et al., 1995, "Structure-activity relationships of dermorphin analogues containing N-substituted amino acids in the 2-position of the peptide sequence," Int. J. Peptide Protein Res. 46:47-55.
Schwesinger, R., 1985, "Extremely strong, non-ionic bases: synthesis and applications," Chimia 39(9):269-72.
Bowman, Russell W., et al., "A Facile Method for the N-Alkylation of .alpha.-Amino Esters," Tetrahedron (1997) vol. 53, No. (46):15787-15798.
Greene, Theodora W., "Protective groups In Organic Synthesis," J. Org. Chem. (1971) vol. 36:282-287.
Miller, Stephen C., et al., "Site-Selective N-Methylation of Peptides on Solid Support," J. Am. Chem. Soc. (1997) vol. 119:2301-2302.
Miller Stephen
Scanlan Thomas S.
Field Bret E.
Green Lora M.
Ricigliano Joseph W.
Sherwood Pamela J.
The Regents of the University of California
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