Mild solid-phase synthesis of aligned, branched triple-helical p

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...

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530334, 530336, 530337, 530356, 530810, 530812, 530816, C07K 104, C07K 106, C07K 1478, C08G 6910

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057262438

ABSTRACT:
A triple-helical polypeptide of the formula: ##STR1## is provided wherein: Z is Hyp or Pro; each X and Y is an amino acid such that (Gly-X-Y).sub.m is a sequence of a collagen cell adhesion site; said X and Y may be the same or different and each (Gly-X-Y) may be the same or different; O is an amino acid having a single side-chain amino group; J is an amino acid capable of acting as a chromophore; U is an amino acid; u=0 or 1; n.ltoreq.30; m.ltoreq.30; m+n.ltoreq.30; and j.gtoreq.1. Methods of making these compounds and intermediates used in the methods, are also provided.

REFERENCES:
patent: 4062746 (1977-12-01), Rich et al.
patent: 4108846 (1978-08-01), Meienhofer
patent: 5576419 (1996-11-01), Fields
J.G. Adamson et al., "Use of Marfey's Reagent to Quantitate Racemization upon Anchoring of Amino Acids to Solid Supports for Peptide Synthesis," Anal. Biochem., 202, 210-214 (1992).
Albericio et al., "Allyl-based orthogonal solid phase Peptide synthesis," Peptides 1992 (Proceedings of the Twenty-Second European Peptide Symposium, Sep. 13-19, 1992, Interlaken, Switzerland), ESCOM, Leiden, pp. 191-193 (1993).
G. Barany et al., "A New Amino Protecting Group Removable by Reduction. Chemistry of the Dithiasuccinoyl (Dts) Function," J. Am. Chem. Soc., 99, 7363-7365 (1977).
K. Barlos et al., "Application of the Trt and Fmoc Groups for the Protection of Polyfunctional .alpha.-Amino Acids," Liebigs. Ann. Chem., 1025-1030 (1987).
B. Brodsky et al., "NMR and CD Studies of Triple-Helical Peptides," Biopolymers, 32, 447-451 (1992).
B.W. Bycroft et al., "A Novel Lysine-protecting Procedure for Continuous Flow Solid Phase Synthesis of Branched Peptides," J. Chem. Soc., Chem. Commun., 778-779 (1993).
M.K. Chelberg et al., "Type IV Collagen-mediated Melanoma Cell Adhesion and Migration: Involvement of Multiple, Distinct Domains of the Collagen Molecule," Cancer Research, 49, 4796-4802 (1989).
M.K. Chelberg et al., "Characterization of a Synthetic Peptide from Type IV Collagen That Promotes Melanoma Cell Adhesion, Spreading, and Motility," J. Cell. Biol., 111,261-270 (1990).
O. Dangles et al., "Selective Cleavage of the Allyl and Allyloxycarbonyl Groups through Palladium-Catalyzed Hydrostannolysis with Tributyltin Hydride. Application to the Selective Protection-Deprotection of Amino Acid Derivatives and in Peptide Synthesis," J. Org. Chem., 52, 4984-4993 (1987).
B.B. Doyle et al., "Collagen Polymorphism: Its Origins in the Amino Acid Sequence," J. Mol. Biol., 91, 79-99 (1975).
J. Engel et al., "The Triple Helix=Coil Conversion of Collagen-Like Polytripeptides in Aqueous and Nonaqueous Solvents. Comparison of the Thermodynamic Parameters and the Binding of Water to (L-Pro-L-Pro-Gly).sub.n and (L-Pro-L-Hyp-Gly).sub.n," Biopolymers, 16, 601-622 (1977).
C.G. Fields et al., "Solid phase peptide synthesis of .sup.15 N-gramicidins A, B, and C and high performance liquid chromatographic purification," Int. J. Peptide Protein Res., 33, 298-303 (1989).
C.G. Fields et al., "Three-dimensional orthogonal solid-phase synthesis of cell-adhesive, triple-helical collagen-model peptides," Peptide Chemistry 1992 (Proceedings of the 2nd Japan Symposium on Peptide Chemistry, Nov. 9-13, 1992, Shizuoka, Japan), ESCOM, Leiden, pp. 14-18 (1993).
C.G. Fields et al., "The Development of High-Performance Liquid Chromatographic Analysis of Allyl and Allyloxycarbonyl Side-Chain-Protected Phenylthiohydantoin Amion Acids," Anal. Biochem., 203, 245-251 (1992).
C.G. Fields et al., "HBTU Activation for Automated Fmoc Solid-Phase Peptide Synthesis," Peptide Research, 4, 95-101 (1993).
C.G. Fields et al., "Edman Degradation Sequence Analysis of Resin-Bound Peptides Synthesized by 9-Fluorenylmethoxycarbonyl Chemistry," Peptide Research, 6, 39-47 (1993).
G.B. Fields et al., "Solid Phase Peptide Synthesis Utilizing 9-Fluorenylmethoxycarbonyl Amino Acids," Int. J. Peptide Protein Res., 35, 161-214 (1990).
G.B. Fields et al., "The Versatility of Solid Phase Peptide Synthesis," in Innovation and Perspectives in Solid Phase Synthesis; R. Epton, Ed.; Solid Phase Conference Coordination, Ltd.: Birmingham, U.K., pp. 241-260, (1990).
G.B. Fields et al., "Optimization Strategies for FMOC Solid-Phase Peptide Synthesis: Synthesis of Triple-Helical Collagen-Model Peptides," in Innovation and Perspective in Solid Phase Synthesis-Peptides, Polypeptides and Oligonucleotides, Abstract No. 118:125044 (1992), R. Epton Ed., Solid Phase Conference Coordination, Ltd.: Birmingham, U.K. (1992).
G.B. Fields et al., "Principles and Practice of Solid-Phase Peptide Synthesis," in Synthetic Peptides: A User's Guide, G.A. Grant, Ed., W.H. Freeman & Co., New York, NY; pp. 77-183, (1992).
H.P. Germann et al., "A Synthetic Model of Collagen: An Experimental Investigation of the Triple-Helix Stability," Biopolymers, 27, 157-163 (1988).
M.R. Ghadiri et al., "A Convergent Approach to Protein Design. Metal Ion-Assisted Spontaneous Self-Assembly of a Polypeptide into a Triple-Helix Bundle Protein," J. Am. Chem. Soc., 114, 825-831 (1992).
U.B. Goli et al., "Synthetic Triple Helical Models for the Collagen Cleavage Site in Interstitial Collagens", MATRIX, 71-72 (1992).
F. Guibe et al., "Use of an Allylic Anchor Group and of its Palladium Catalyzed Hydrostannolytic Cleavage in the Solid Phase Synthesis of Protected Peptide Fragments," Tetrahedron Letters, 30, 2641-2644 (1989).
N. Jentoft et al., "Labeling of Proteins by Reductive Methylation Using Sodium Cyanoborhydride," J. Bio. Chem., 254, 4359-4365 (1979).
P. Lloyd-Williams et al., "Solid-Phase Synthesis of Peptides Using Allylic Anchoring Groups. An Investigation of Their Palladium-Catalyzed Cleavage," Tetrahedron Letters, 32, 4207-4210 ( 1991 ).
R. Matsueda et al., "3-Nitro-2-Pyridinesulfenyl (Npys) Group. A Novel Selective Protecting Group Which Can Be Activated for Peptide Bond Formation," Int. J. Peptide Protein Res., 16, 392-401 (1980).
D.G. Mullen et al., "A New Fluoridolyzable Anchoring Linkage for Orthogonal Solid-Phase Peptide Synthesis: Design, Preparation, and Application of the Pentanedioic Acid Monoamide (Pbs) Handle," J. Org. Chem., 53, 5240-5248 (1988).
M. Mutter et al., "A Chemical Approach to Protein Design-Template-Assembled Synthetic Proteins (TASP)," Angew. Chem. Int. Ed. Engl., 28, 535-554 (1989).
B.R. Olsen et al., "The Synthetic Polytripeptides (Pro-Pro-Gly).sub.10 and (Pro-Pro-Gly).sub.20 Form Micro-crystalline Structures Similar to Segmental Structures formed by Collagen," J. Mol. Biol., 57, 589-595 (1971).
A. Patchornik et al., "Photosensitive Protecting Groups," J. Am. Chem. Soc., 92, 6333-6335 (1970).
W. Roth et al., "Die Struktur kollagenahnlicher Homo- und Heteropolytripeptide, 4.sup.a). Polytripeptide durch repetitive Peptidsynthese und Verbruckung von Oligopeptiden," Makromol. Chem., 180, 905-917 (1979).
W. Roth et al., "Triple Helix-Coil Transition of Covalently Bridged Collagenlike Peptides," Biopolymers, 19, 1909-1917 (1980).
S. Sakakibara et al., "Synthesis of Poly-(L-prolyl-L-prolylglycyl) of Defined Molecular Weight," Bull. Chem. Soc. Jpn., 41, 1273 (1968).
W.J.G. Schielen et al., "Use of Mpc-amino acids in solid phase peptide synthesis leads to improved coupling efficiencies," Int. J. Peptide Protein Res., 37, 341-346 (1991).
J. Shao et al., "A Test-Case for the 1-(1-Adamantyl)-1-Methylethoxycarbonyl (ADPOC) Group: Solid-Phase Synthesis of LH-RH Using N.sup.a -ADPOC Protection and an Acid Labile Handle," Tetrahedron Letters., 32, 345-346 (1991).
K. Sutoh et al., "Conformational Change of the Triple-Helical Structure. I. Synthesis of Model Peptides of Collagen by the Solid-Phase Method," Biopolymers, 13, 2385-2390 (1974).
K. Sutoh et al., "Conformational Change of the Triple-Helical Structure. II. Conformation of (Pro-Pro-Gly).sub.n and (Pro-Pro-Gly).sub.n (Ala-Pro-Gly).sub.m (Pro-Pro-Gly).sub.n in an Aqueous Solution," Biopolymers, 13, 2391-2404 (1974).
J.P. Tam et al., "Strong Acid Deprotection of Synthetic Peptides: Mechanisms and Methods," in The Peptides, vol. 9, Academic Press, Inc.; pp. 185-248, (1967).
S. Thakur et al., "Influence of Different Tripeptides on the Stability o

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