Method for inverse solid phase synthesis of peptides

Details Method for inverse solid phase synthesis of peptides Method for inverse solid phase synthesis of peptides

2007-05-08

2007-05-08

Lukton, David (Department: 1654)

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

C530S334000, C530S335000

Reexamination Certificate

active

10156669

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]-[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)-[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]-[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.

REFERENCES:
patent: WO-90/05738 (1990-05-01), None
patent: WO-93/05065 (1993-03-01), None
Matseuda (J. Am. Chem Soc. 97, 2573-75, 1975).
Maruyama, Hiroshi (Bulletin of the Chemical Society of Japan 49(8), 2259-67, 1976).
Matsueda, Rei, “Solid Phase Peptide Synthesis by Oxidation-Reduction Condenstation. 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 Memetics”,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),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, 234-235.

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