Cyclization of peptides
AssigneeArmour Pharmaceutical Company
InventorsJohn L. Hughes, Jay K. Seyler, Robert C. Liu
Life of this patent
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Abstract
The synthesis of a disulfide cyclic peptide by preparing an intermediate peptide containing an amino terminal cystine residue and a cysteine residue located in a position within the amino acid sequence, to give a desired peptide, and placing such intermediate peptide in a solution substantially free of oxygen at a pH of from about 5 to 10 until rearrangement takes place to yield a cyclic disulfide peptide and to displace a molecule of cysteine from the amino terminal cysteine residue. The disclosure also embraces said intermediate peptides as new compounds and the processes by which they are prepared.
Claims21
In a process for preparing a peptide having a disulfide ring structure, the step of holding a peptide which contains an amino terminal cystine residue and a cysteine residue located in a position within the amino acid sequence in a solution substantially free of oxygen until rearrangement has taken place to yield a cyclic disulfide peptide.
A process as set forth in clain 1 in which said peptide is:
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A peptide having an amino acid sequence the same as that of a natural calcitonin and which contains an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
A peptide having an amino acid sequence which is the same as that of oxytocin and containing an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
a peptide having an amino acid sequence the same as that of vasopressin and containing an amino terminal cystine moiety and a cysteine moiety within said sequence having a free sulfhydryl function.
A peptide having an amino acid sequence the same as that of a natural calcitonin and which contains an amino terminal cystine moiety and an intermediate cysteine moiety having its sulfhydryl function protected by a group selected from the class consisting of benzyl, 4-methoxybenzyl, 4-methylbenzyl, 3,4-dimethylbenzyl, 4-chlorobenzyl, 2,6-dichlorobenzyl, 4-nitrobenzyl, benzylhydryl, tertiary butylthio, and isopropylthio.
Dependencies are inferred from the claim text.