Cyclic peptide mixtures via side chain or backbone attachment an

Chemistry: analytical and immunological testing – Involving an insoluble carrier for immobilizing immunochemicals

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

436524, 436526, 436528, 530317, 530333, 530334, G01N 33543, C07C 512, C07C 700, C07C 1700

Patent

active

060080582

ABSTRACT:
A method of preparing cyclic peptide mixtures via side chain or backbone and solid phase synthesis. The cyclic peptide mixtures form libraries that are useful for screening purposes featuring the attachment of an amino acid to a solid support through its side chain or backbone in order to mimic solution cyclization procedures with linear peptides. In the preferred embodiment, Boc chemistry is used for peptide synthesis, wherein the initial attachment of a trifunctional amino acid is by the aspartyl side chain (with OFm for alpha-carboxyl protection). Cyclization is performed using uronium reagents with racemization suppressant, and a strong acid (HF) is used for deprotection and cleavage. The strategy has been used for the preparation of a series of cyclic peptide mixtures. The procedure is expandable to include at least twenty different amino acids at each position (except the resin linked position where most attachments are by Asp, Lys, Glu, or Orn). The cyclic peptide mixtures vary in ring size from about four to about twelve residues.

REFERENCES:
patent: 4659691 (1987-04-01), Veber et al.
patent: 4663309 (1987-05-01), Kaiser et al.
patent: 4757048 (1988-07-01), Lewicki et al.
patent: 4778784 (1988-10-01), Dreesman et al.
patent: 4786684 (1988-11-01), Glass
patent: 4914188 (1990-04-01), Dumont et al.
patent: 4959352 (1990-09-01), Felix et al.
patent: 5010175 (1991-04-01), Rutter et al.
patent: 5043322 (1991-08-01), Rivier et al.
patent: 5064939 (1991-11-01), Rivier et al.
patent: 5084442 (1992-01-01), Felix et al.
patent: 5120859 (1992-06-01), Webb
patent: 5134123 (1992-07-01), Branca et al.
patent: 5143854 (1992-09-01), Pirrung et al.
patent: 5149778 (1992-09-01), Adams et al.
patent: 5164481 (1992-11-01), Lacroix et al.
patent: 5166394 (1992-11-01), Breipohl
patent: 5169862 (1992-12-01), Burke, Jr. et al.
patent: 5175144 (1992-12-01), Basava et al.
patent: 5182263 (1993-01-01), Danno et al.
patent: 5182366 (1993-01-01), Huebner et al.
patent: 5186824 (1993-02-01), Anderson et al.
patent: 5194392 (1993-03-01), Geysen
"Simultaneous Multiple Synthesis and Selective Conjugation of Cyclized Peptides Derived From A Surface Loop of a Meningococcal Class 1 Outer Membrane Protein", by H.F. Bruggie, in Int. J. Peptide Protein Res., vol. 43, pp. 166-172, 1994.
"Multiple Release of Equimolar Amounts of Peptides from a Polymeric Carrier Using Orthogonal Linkage-Cleavage Chemistry" by M. Lebl, in Int. J. Peptide Protein Res. vol. 41, pp. 201-203, 1993.
Meldal, "Multiple Column Peptide Synthesis: Development and Application", Peptides, pp. 61-62, 1992.
Lebl and Hruby, "synthesis of Cyclic Peptides by Solid Phase Methodology", Tetrahedron Letters, vol. 25, No. 20, pp. 2067-2068, 1984.
Arno F. Spatola, Krzysztof Darlak, and Peteris Romanovskis Cyclic Peptide Libraries: Reducing Epimerization in Medium Sized Rings During Solid Phase Synthesis:, Tetrahedron Letters, pp. 37, 591-594, (1996).
O'Neil, Hoess, Jackson, Ramachandran, Mousa, and Degrado, "Identification of Novel Peptide Antagonists for GPIIb/IIIa From a Conformationally Constrained Phage Peptide Library", Proteins, vol. 14, No. 4, pp. 509-515, 1992.
"Biologically Active Conformations of Thymopentin" by Heavner, G.A. et al., Int. J. Peptide Protein Res. 37, 1991, 198-209.
"Solid Phase Synthesis of a Cyclic peptide Using Fmoc Chemistry", by J.S. McMurray, in Tetrahedron Letters, vol. 32, No. 52, pp. 7679-7682, 1991.
"Macrocyclization Equilibria of Polypeptides" by M. Mutter in Journal of American Chemical society, vol. 99, No. 25, Dec. 7, 1977.
Spanevello et al: Synthesis of Novel High Potent Cyclic-Hexapeptide Analogues of Somatostatin. Potential Application of Orthogonal Protection for Affinity Chromatography. Tetrahedron Letters, vol. 32, 1991, pp. 4675-4678.
Trzeciak et al: Synthesis of `Head-to-Tail` Cyclized Peptides on Solid Supports by Fmoc Chemistry. Tetrahedron Letters, vol. 33, 1992, pp. 4557-4560.
Jian J. Chen, Lynn M. Teesch, and Arno F. Spatola, "Using Cyclic Peptide Mixtures as Probes for Metal Ion Host-Guest Interactions", Letters in Peptide Science, 3 17-24 (1996); and.
Birkett et al., "Determination of Enzyme Specificity in a Complex Mixture of Peptide Substrates by N-Terminal Sequence Analysis," Analytical Biochemistry, v. 196, pp. 137-143 (1991).
Kerr et al., "Encoded Combinatorial Peptide Libraries Containing Non-Natural Amino Acids," Journal of American Chemical Society, v. 155, pp. 2529-2531 (1993).
Felix et al., "Applications of BOP reagent in solid phase synthesis," Int. J. Peptide Protein Res., v. 31, pp. 231-238 (1988).
Houghten et al., "The Use of Sythetic Peptide Combinatorial Libraries for the Identification of Bioactive Peptides," Peptide Research v. 5 #6, pp. 351-358 (1992).
Jung and Beck-Sickinger, "Multiple Peptide Synthesis Methods and their applications," Angewandte Chemie International Edition in English, v. 3 #4, pp. 367-486 (1992).
Scott, "Discovering peptide ligands using epitope libraries" Tibs, v. 17 pp. 240-245 (1992).
Houghten et al., "Generation and use of synthetic peptide combinatorial libraries for basic research and drug discovery," Nature, v. 354, pp. 84-86 (1991).
Lam et al., "A new type of synthetic peptide library for identifying ligand-binding activity", Nature, v. 354, pp. 82-84 (1991).
Furka et al., "General Method for rapid synthesis of multi-component peptide mixtures," Im. J. Peptide Protein Res., v. 37 pp. 487-493 (1991).
Frank, "Spot Synthesis: Positionally addressable, parallel chemical synthesis on membrane supports," Peptides, pp. 59-62 (1992).
Sebestyen et al., "Effieciency and limitations of the `portioning-mixing` peptide synthesis," Peptides, pp. 63-69 (1992).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Cyclic peptide mixtures via side chain or backbone attachment an 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 peptide mixtures via side chain or backbone attachment an, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Cyclic peptide mixtures via side chain or backbone attachment an will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-2381623

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.