Conformationally restricted mimetics of gamma turns and peptides

Details Conformationally restricted mimetics of gamma turns and peptides Conformationally restricted mimetics of gamma turns and peptides

1995-06-06

1997-09-30

Hutzell, Paula K.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Cyclic peptides

514 11, 530323, 530333, A61K 3812, C07K 500

Patent

active

056726813

ABSTRACT:
The invention provides materials and methods for synthesizing novel reverse turn mimetics, as well as peptides containing the same. Also provided are novel synthetic nonpeptide therapeutic molecules designed upon the interactions between reverse turn mimetics or peptides containing the same, and receptors, antibodies, or enzymes.

REFERENCES:
patent: 4699898 (1987-10-01), Gottlieb
patent: 4908203 (1990-03-01), Thornton
Kahn and Chen, "Methodology for the Synthesis of Mimetics of Peptide .beta.-turns," Tetrahedron Letters 28(15): 1623-1626, 1987.
Kahn et al., "Nonpeptide Mimetics of .beta.-Turns: A Facile Oxidative Intramolecular Cycloaddition of an Azodicarbonyl System," Journal of the American Chemical Society 110: 1638-1639, 1988.
Kahn et al., "The Design and Synthesis of Mimetics of Peptide .beta.-turns," Journal of Molecular Recognition 1(2): 75-79, 1988.
Kahn and Bertenshaw, "The Incorporation of .beta.-Turn Prosthetic Units Into Merrifield Solid Phase Peptide Synthesis," Tetrahedron Letters 30(18): 2317-2320, 1989.
Kahn et al., "The Design and Synthesis of a Nonpeptide Mimic of Erabutoxin," Heterocycles 25: 29-31, 1987.
Kahn and Devens, "The Design and Synthesis of a Nonpeptide Mimic of an Immunosuppressing Peptide," Tetrahedron Letters 27(40): 4841-4844, 1986.
Ball and Alewood, "Conformational Constraints: Nonpeptide .beta.-Turn Mimics," Journal of Molecular Recognition 3(2): 55-64, 1990.
Freidinger et al., "Bioactive Conformation of Luteinizing Hormone-Releasing Hormone: Evidence from a Conformationally Constrained Analog," Science 210: 656-658, 1980.
Kemp and Stites, "A convenient preparation of derivatives of 3(S)-amino-10(R)-carboxy-1,6-diaza-cyclodeca-2,7-dione. The dilactam of L-.alpha., .gamma.-diaminobutyric acid and D-glutamic acid: a .beta.-turn template," Tetrahedron Letters 29(40): 5057-5060, 1988.
Miller et al., "Synthesis of .beta.-Lactams from Substituted Hydroxamic Acids," Journal of American Chemical Society 102: 7026-7032, 1980.
Olson et al., "Design and Synthesis of a Protein .beta.-Turn Mimetic," J. Am. Chem. Soc. 112: 323-333, 1990.
Arrhenius and Satterthwait, "The substitution of an amide-amide backbone hydrogen bond in an .alpha.-helical peptide with a covalent hydrogen bond mimic," in Proceedings of the American Peptide Symposium, 1990, pp. 870-872.
Carpino et al., "((9-Fluorenylmethyl)oxy)carbonyl (FMOC) Amino Acid Fluorides. Convenient New Peptide Coupling Reagents Applicable to the FMOC/tert-Butyl Strategy for Solution and Solid-Phase Syntheses," J. Am. Chem. Soc. 112: 9651-9652, 1990.
Chang et al., "A Potent Nonpeptide Cholecystokinin Antagonist Selective for Peripheral Tissues Isolated from Aspergillus alliaceus," Science 230:177-179, 1985.
Chen et al., "Design and synthesis of a CD4 .beta.-turn mimetic that inhibits human immunodeficiency virus envelope glycoprotein gp120 binding and infection of human lymphocytes," Proc. Natl. Acad. Sci. USA 89: 5872-5876, 1992.
Chipkin et al., "Analgesics," Ann. Rep. Med. Chem. 23: 11-18, 1988.
Corey and Fuchs, "A Synthetic Method for Formyl.fwdarw.Ethynyl Conversion (RCHO.fwdarw.RC.tbd.CH or RC.tbd.CR')," Tetrahedron Lett. 36: 3769-3772, 1972.
Fauchere, J., "Elements for the Rational Design of Peptide Drugs," Adv. in Drug. Res. 15: 29-69, 1986.
Ferreira et al., "Isolation of Bradykinin-Potentiating Peptides from Bothrops jararaca Venom," Biochemistry 9: 2583, 1970.
Gilon et al., "Backbone Cyclization: A New Method for Conferring Conformational Constraint on Peptides," Biopolymers 31: 745-750, 1991.
Goel et al., "N-tert-Butoxycarbonyl-L-Leucinal (Carbamic acid, (1-formyl-3-methylbutyl)-,1,1-dimethylethyl ester, (S)-)," Org. Syn. 67: 69-75, 1988.
Gribble and Nutaitis, "Sodium Borohydride in Carboxylic Acid Media. A Review of the Synthetic Utility of Acyloxyborohydrides," Org. Prep. Proced. Int. 17: 317-384, 1985.
Hart and Ha, "The Ester Enolate-Imine Condensation Route to .beta.-Lactams," Chem. Rev. 89: 1447-1465, 1989.
Hoffman et al., "The Preparation of 2-Hydrazinyl Esters in High Optical Purity from 2-Sulfonyloxy Esters," Tetrahedron Letters 31(21): 2953-2956, 1990.
House and Rasmusson, "Stereoselective Synthesis of .alpha.-Substituted .alpha.,.beta.-Unsaturated Esters," J. Org. Chem. 26: 4278-4281, 1961.
Hruby et al., "Emerging approaches in the molecular design of receptor-selective peptide ligands: conformational, topographical and dynamic considerations," Biochem. J. 268: 249-262, 1990.
Hruby, V., "Implications of the X-ray structure of deamino-oxytocin to agonist/antagonist-receptor interactions," Trends Pharmacol. Sci. 8: 336-339, 1987.
Krstenansky et al., "A New Approach to Conformationally Restricted Peptide Analogs: Rigid .beta.-Bends. 1. Enkephalin as an Example," Biochem. Biophys. Res. Commun. 109(4): 1368-1374, 1982.
Lindlar, H., "Ein Neuer Katalysator fur selektive Hydrierungen," Helv. Chim. Acta 35(57): 446-450, 1952.
Marshall et al., "Peptide Conformation and Biological Activity," Ann. Rep. Med. Chem. 13: 227-238, 1978.
Morgan et al., "Approaches to the Discovery of Non-Peptide Ligands for Peptide Receptors and Peptidases," Ann. Rep. Med. Chem. 24: 243-252, 1989.
Rajeswari et al., "A New Synthesis of Amides from Acyl Fluorides and N-Silylamines," Tetrahedron Letters 28(43): 5099-5102, 1987.
Romer et al., "An opioid benzodiazepine," Nature 298: 759-760, 1982.
Salzmann et al., "A Stereocontrolled Synthesis of (+)-Thienamycin," J. Am. Chem. Soc. 102: 6161-6163, 1980.
Sargovi et al., "Design and Synthesis of a Mimetic from an Antibody Complementarity-Determining Region," Science 253: 792-793, 1991.
Sasaki and Coy, "Solid Phase Synthesis of Peptides Containing the CH.sub.2 NH Peptide Bond Isostere," Peptides 8: 119-121, 1987.
Satterthwait et al., "Polypeptides stabilized by covalent hydrogen bond replacements," Chem. Abst. 112: 179892y, 1990.
Spatola, A., "Peptide Backbone Modifications: A Structure-Activity Analysis of Peptides Containing Amide Bond Surrogates. Conformational Constraints, and Rela . . . ," in Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins 7, Weinstein, Ed., Marcel Dekker, New York, 1983, pp. 276-357.
Valle et al., "Crystal-state structural analysis of two .gamma.-lactam-restricted analogs or Pro-Leu-Gly-NH.sub.2," Int. J. Peptide Protein Res. 33: 181-190, 1989.
Wasserman et al., "Transamidation Reactions Using .beta.-Lactams. The Synthesis of Homaline," Tetrahedron Lett. 23: 465-68, 1982.
Williams et al., "Syntheses and X-ray Crystal Structure Determination of 1,3-Bridged Beta-Lactams," Journal of the American Chemical Society 111: 1073-1081, 1989.

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