Process for peptide segment condensation

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Synthesis of peptides

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530338, 530339, 562443, 562553, 564138, 564164, 564193, 564198, C07C23102, C07K 108

Patent

active

055021654

ABSTRACT:
The present invention is drawn to a process for forming an amide bond linkage comprising reacting a carboxylic acid and an amine in a two-phase mixture of water and an organic solvent selected from an oxygenated organic solvent or an aromatic solvent in the presence of a coupling reagent and an additive. This process is useful for making ubiquitous amides and polypeptides having various biological activities.

REFERENCES:
patent: 3870694 (1975-03-01), Fujino et al.
patent: 4755591 (1988-07-01), Konig et al.
patent: 5166394 (1992-11-01), Breipohl et al.
Nozaki, S. et al., Chem. Lett. 1977, 1057-1058, entitled, Rapid Peptide Synthesis in Liquid Phase. Preparation of Angiotension II as an Example.
Nozaki, S. & Muramatsu, I., Bull. Chem. Soc. Japan, 1982, 55,2165-2168, entitled, Rapid Peptide Synthesis in Liquid Phase, Preparation of Angiotension II and Delta-sleep-inducing Peptide by the "Hold-in-Solution" Method.
Schneider, C. H. and Wirz, W., Helv. Chim. Acta, 1972, 55, 1062-1074, entitled, Antigen Synthesis: The Preparation of Selected Dodecapeptide Carriers with Systematically Altered Structures by a Two-Phase Method.
Sheehan, J. C., et aL., J. Am. Chem. Soc., 1965, 87, 2492-2493, entitled, A Rapid Synthesis of Oligopeptide Derivatives Without Isolation of Intermediates.
Fujino, M. et al., Chem. Pharm Bull., 1974, 22(8), 1857-1863, entitled, The Use of N-Hydroxy-5-norbornene-2,3-dicarboximide Active Esters in Peptide Synthesis.
Carpino, L. A., J. Am. Chem. Soc., 1993, 115, 4397-4398, entitled, 1-Hydroxy-7-azabenzotriazole. An Efficient Peptide Coupling Additive.

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