Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides
Reexamination Certificate
2007-07-17
2007-07-17
Lukton, David (Department: 1654)
Chemistry: natural resins or derivatives; peptides or proteins;
Peptides of 3 to 100 amino acid residues
Synthesis of peptides
C530S333000, C530S345000
Reexamination Certificate
active
10848964
ABSTRACT:
The present invention provides a process for preparing a peptide of formula I):in-line-formulae description="In-line Formulae" end="lead"?Sub-[L]-[N(R1)-A-C(O)]p—[NH-A-C(O)]n+m—OH (I)in-line-formulae description="In-line Formulae" end="tail"?comprising:(a) reacting an immobilized compound of formula (II):in-line-formulae description="In-line Formulae" end="lead"?Sub-(L)-[N(R1)-A-C(O)]p—[NH-A-C(O)]n—OH (II)in-line-formulae description="In-line Formulae" end="tail"?with an amino acid ester or peptide derivative of formula (III):in-line-formulae description="In-line Formulae" end="lead"?H—[NH-A-C(O)]m—O(tBu) (III)in-line-formulae description="In-line Formulae" end="tail"?in the presence of a coupling agent to yield a peptide compound of general formula (IV):in-line-formulae description="In-line Formulae" end="lead"?Sub-[L]-[N(R1)-A-C(O)]p—[NH-A-C(O)]n+m—O(tBu); (IV)in-line-formulae description="In-line Formulae" end="tail"?(b) removing the tBu (t-butyl) group to produce a solid-support bound carboxylic acid or peptide derivative of general formula (I);wherein n is a positive integer, e.g., 1–10, preferably 1–5; m is a positive integer, and P is 0–1.
REFERENCES:
Maruyama, H. , et al., “Solid Phase Peptide Synthesis by Oxidation-Reduction Condensation. Synthesis of Adrenocorticotropin(1-24)by Chain Elongation at the Carboxyl End on Solid Support”,Bulletin of the Chemical Society of Japan, 49(8), (1976), 2259-2267.
Matsueda, R. , “Solid Phase Peptide Synthesis by Oxidation-Reduction Condensation”,Journal of the American Chemical Society 97:9, Communications to the Editor, (Apr. 30, 1975), 2573-2575.
Matsueda, Rei , “Solid Phase Peptide Synthesis by Oxidation-Reduction Condensation. Synthesis of LH-RH by Fragment Condensation on Solid Support”,Bulletin of the Chemical Society of Japan, vol. 46, No. 10, (1973), 3240-3247.
Rai, Aman , et al., “A Dde Resin Based Strategy for Inverse Solid-Phase Synthesis of Amino Terminated Peptides, Peptide Mimetics and Protected Peptide Intermediates”,Journal of Peptide Science, (2004), 5.
Sasubilli, Ramakrishna , et al., “General Inverse Solid-Phase Synthesis Method for C-Terminally Modified Peptide Mimetics”,J. Comb. Chem., 6, (2004), 911-915.
Gutheil, William G., et al., “N-to-C Solid-Phase Peptide and Peptide Tirflouromethylketone Synthesis Using Amino Acid tert-Butyl Esters”,Chem. Pharm. Bull.vol. 50, No. 5, (Feb. 20, 2002), pp. 688-691.
Xu, Qingchai, et al., “A New Strategy for Inverse Solid-Phase Peptide Synthesis”,Peptides: The Wave of the Future; American Peptide Society, 2001, pp. 234-235.
Lukton David
Schwegman Lundberg Woessner & Kluth P.A.
The Curators of the University of Missouri
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