Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Cyclic peptides
Patent
1997-11-19
2000-02-29
Moezie, F. T.
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Cyclic peptides
514 9, 514 11, 530333, 530336, A61K 3812, C07K 700
Patent
active
060310731
ABSTRACT:
This invention relates generally to cyclic polypeptides comprising a thioether linkage and methods for their preparation. More particularly, this invention relates to halogenated polypeptides having at least one haloalanine-like amino acid, and methods for their preparation which involve converting the hydroxyl group (i.e., --OH) of a serine-like amino acid to a halo group (i.e., --X where X is Cl, Br, or I) with the aid of a phosphorus-based halogenation reagent such as a triphenylphosphine dihalide (i.e., (C.sub.6 H.sub.5).sub.3 PX.sub.2, wherein X is Cl, Br, or I), a triphenylphosphite dihalide (i.e., (C.sub.6 H.sub.5 O).sub.3 PX.sub.2, wherein X is Cl, Br, or I), or a mixture of triphenylphosphine or triphenylphosphite with a halohydrocarbon (i.e., "halo-conversion"). This invention also relates to cyclic polypeptides having at least one polypeptide loop comprising a thioether linkage, and methods for their preparation which employ halogenated polypeptides and which involve intramolecular alkylation of the thiol group of a cysteine-like amino acid by the halo group of a haloalanine-like amino acid under suitable basic conditions to form a thioether linkage (i.e., "cyclization").
REFERENCES:
patent: 5268454 (1993-12-01), Barstad et al.
patent: 5817752 (1998-10-01), Yu
Appel et al., "Notiz uber ein bequemes verfahren zur darstellung von dichlorphosphoranen" Chem. Ber. (1977) 110:2382-2384. A partial English translation is enclosed.
Appel et al., "Reaktionen im zweikomponentensystem triphenylphospin/tetrachlormethan" Chem. Ber. (1976) 109:58-70. An English abstract is included on p. 58 of this document.
Balaram, "The design and construction of synthetic protein mimics" Pure & Appl. Chem. (1992) 64:1061-1066.
Blondelle et al., "Novel antimicrobial compounds identified using synthetic combinatorial library technology" Trends in Biotechnology (1996) 14:60-65.
Burgess et al., "Comparison of the effects of (2S,3S)-2,3-methanomethionine, (2R,3R)-2,3-methanomethionine, and (2R,3R)-2,3 methanophenylalanine on the conformations of small peptides" J. Am. Chem. Soc. (1995) 117:3808-3819.
Cheung et al., "Chloroalanyl and propargylglycyl dipeptides. Suicide substrate containing antibacterials" J. Med. Chem. (1983) 26:1733-1741.
Cheung et al., "Chloroalanyl antibiotic peptides: Antagonism of their antimicrobial effects by L-alanine and L-alanyl peptides in gram-negative bacteria" J. Med. Chem. (1986) 29:2060-2068.
Coutts et al., "Pharmacological intervention in antibody mediated disease" Lupus (1996) 5:158-159.
Dintzis, "Rational design of conjugate vaccines" Pediatric Res. (1992) 32:376-385.
Ellman, "Tissue sulfhydryl groups" Arch. Biochem. Biophys. (1959) 82:70-77.
Fields et al., "Solid phase peptide synthesis utilizing 9-fluorenylmethoxycarbonyl amino acids" Int. J. Pept. Protein Res. (1990) 35:161-214.
Fischer, "Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine and peptide synthesis" Tetrahedron Lett. (1992) 49:7605-7608.
Fukase et al., "Synthetic study on peptide antibiotic nisin. II. The synthesis of Ring B" Bull. Chem. Soc. Jpn. (1985) 59:2505-2508.
Hinds et al., "Synthesis, conformational properties, and antibody recognition of peptides containing .beta.-turn mimetics based on .alpha.-alkylproline derivatives" J. Med. Chem. (1991) 34:1777-1789.
Hruby et al., "Design of novel synthetic peptides including cyclic conformationally and topgraphically constrained analogs" Methods in Molecular Biology (1994) 35:201-240.
Hruby et al., "Emerging approaches in the molecular design of receptor-selective peptide ligands: conformational, topographical and dynamic considerations" Biochem. J. (1990) 268:249-262.
Jack et al., "Unique peptide modifications involved in the biosynthesis of lantibiotics" Trend in Biotechnology (1995) 13:269-278.
Jones et al., "Conjugates of double-stranded oligonucleotides with poly(ethylene glycol) and keyhold limpet hemocyanin: A model for treating systemic lupus erythematosus" Bioconjugate. Chem. (1994) 5:390-399.
Jones et al., "Immunospecific reduction of antioligonucleotide antibody-forming cells with a tetrakis-ogigonucleotide conjugate (LJP 394), a therapeutic candidate for the treatment of lupus nephritis" J. Med. Chem. (1995) 38:2138-2144.
Jost et al., "Amino acids and peptides. LXXIV. Derivatives of L-cystathionine suitable for peptide synthesis" Collect. Czech. Commun. (1967) 32:2485-2490.
Cavelier-Frontin et al. "New diastereoselective synthesis of protected meso-lanthionine with discrimination of the chiral centers" Tetrahedron Asymmetry (1992) 3:85-94.
Jung, "Lantibiotics-ribosomally synthesized biologically active polypeptides containing sulfide bridges and .alpha.,.beta.-didehydroamino acids" Angew. Chem. Int. Ed. Engl. (1991) 30:1051-1192.
Kaiser et al., "Color test for detection of free terminal amino groups in the solid-phase synthesis of peptides" Anal. Biochem. (1970) 34:595-598.
Kataoka et al., "The utility of side-chain cyclization in determining the receptor-bound conformation of peptides: Cyclic tripeptides and angiotensin II" Biopolymers (1992) 32:1519-1533.
Katz et al., "Structure-based design of high affinity streptavidin binding cyclic peptide ligands containing thioether cross-links" J. Am. Chem. Soc. (1995) 117:8541-8547.
Lebl et al., "Synthesis of cyclic peptides by solid phase methodology" Tetrahedron Lett. (1984) 25:2067-2068.
Liu et al., "New procedures for preparation and isolation of conjugates of proteins and a synthetic copolymer of D-amino acids and immunochemical characterization of such conjugates" Biochemistry (1979) 18:690-697.
Mayer et al., "An alternative solid-phase approach to C.sub.1 -oxytocin" Tetrahedron Lett. (1995) 36:7387-7390.
Mosberg et al., "Dithioether-containing cyclic peptides" J. Am. Chem. Soc. (1985) 107:2986-2987.
Osapay et al., "New application of peptide cyclization of an oxime resin (the PCOR method): Preparation of lanthionine peptides" J. Chem. Soc. Chem. Commun. (1993):1599-1600.
Polinsky et al., "Synthesis and conformational properties of the lantionine-bridged opioid peptide [D-Ala.sub.L .sup.2,Ala.sub.L .sup.5 ]enkephalin as determined by NMR and computer simulations" J. Med. Chem. (1992) 35:4185-4194.
Probert et al., "Lanthionines for solid phase synthesis" Tetrahedron Lett. (1996) 37:1101-1104.
Safar et al., "The carba-modification of cystine-containing peptides: Synthesis of selectively protected cystathionines and their incorporation in the oxytocin molecule" Peptides: Chemistry, Structure and Biology (Hodges, R.S. and Smith, J. A. Eds.) Escom, Leiden, The Netherlands, (1994) 119-120.
Sahl et al., "Biosynthesis and biological activities of lantibiotics with unique post-translational modifications" Eur. J. Biochem. (1995) 230:827-853.
Shao et al., "A facile synthesis of orthogonally protected stereoisomeric lanthionines by regioselective ring opening of serine .beta.-lactone derivatives" J. Org. Chem. (1995) 60:2956-2957.
Stewart et al., Solid Phase Peptide Synthesis, 2nd., Pierce Chemical Co.: Rockford, IL., (1984), p. 82.
Tam, "Synthesis and applications of branched peptides in immunological methods and vaccines" Peptides: Synthesis, Structures, and Applications (Gutte ed.) Academic Press, San Diego, (1995) 455-500.
Tam, "Synthetic peptide vaccine design: Synthesis and properties of a high-density multiple antigenic peptide systems" Proc. Natl. Acad. Sci. USA. (1988) 85:5409-5413.
Toniolo et al., "Structures of peptides from .alpha.-amino acids methylated at the .alpha.-carbon" Biopolymers (1993) 33:1061-1072.
Toniolo, "Conformationally restricted peptides through short-range cyclizations" Int. J. Peptide Protein Res. (1990) 35:287-300.
Wunsch et al., "1-(tert-butylthio)-1.2-hydrazinedicarboxylic acid derivatives. New reagents for the introduction of the S-tert-butylthio group into cysteine and cysteine derivatives" Hoppe-Seyler's Z. Physiol. Chem. (1982), 363:1461-1464.
La Jolla Pharmaceutical Company
Moezie F. T.
LandOfFree
Cyclic polypeptides comprising a thioether linkage and methods f does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Cyclic polypeptides comprising a thioether linkage and methods f, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cyclic polypeptides comprising a thioether linkage and methods f will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-684019