EP0097994A2
Expired / Lapsed
EP
⏱️ 0.0 years remaining
Method for the solid-phase synthesis of retro-inverso polypeptides
Assignee: Sclavo SpA
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Filing: 1983-06-17
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Granted: —
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Expires: 2003-06-17
Abstract
Abstract This invention relates to a method for the solid-phase synthesis of polypeptides containing retro-inverted peptide bonds, using polydimethylacrylamide-co-acryloylsarcosi- methylester resin cross-linked with N, N'-ethylene-bisacrylamide as the insoluble support for lengthening the polypeptide chain in stages by the addition of suitable amino acid derivatives and/or peptides in succession. In particular, the method described in the present invention allows the easy preparation, on the polymer matrix, of monoacylated gem-diamino residues using the reagent I, I-bis (trifluoroace- toxy) iodobenzene in mixed aqueous-organic solvents.
Inventors
- 👤 Antonello Pessi
- 👤 Massimo Pinori
- 👤 Antonio Silvio Verdini
- 👤 Giuseppe Claudio Viscomi
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-27 08:49
CPC Classifications
C; C07; C07K; C07K1/00; C07K1/04; C07K1/042; C07K5/00; C07K5/02; C07K5/0212
Claims Analysis
Total Claims: 3
Claim 1
Independent Claim
139 words
A process for producing polypeptides containing one or more retro-inverted amide bonds, entirely in the solid phase, comprising: a) using the resin polydimethylacrylamide-co-acryloylsarcosine methylester, cross-linked with N,N'-ethylene-bis-acrylamide as the insoluble support for elongating the polypeptide chain in stages; b) choosing a synthesis strategy which comprises assembling the polypeptide chains starting from the C-terminal residue by successive condensation of suitable derivatives of amino acids and/or peptides and of coinpounds corresponding to general formula: where Z and Z', which can be the same or different, indicate the side-chain groups of the amino acids commonly present in natural polypeptide molecules; c) using the reagent I,I-bis(trifluoroacetoxy)iodobenzene for the direct conversion of chain-terminal primary carboxyamide groups into amines; d) finally simultaneously releasing the entire peptide from the resin, the terminal NH 2 protector groups and the lateral functionalities compatible with the release conditions used.
Claim 2
Dependent Claim
139 words
A process for producing polypeptides containing one or more retro-inverted amide bonds, entirely in the solid phase, comprising: a) using the resin polydimethylacrylamide-co-acryloylsarcosine methylester, cross-linked with N,N'-ethylene-bis-acrylamide as the insoluble support for elongating the polypeptide chain in stages; b) choosing a synthesis strategy which comprises assembling the polypeptide chains starting from the C-terminal residue by successive condensation of suitable derivatives of amino acids and/or peptides and of coinpounds corresponding to general formula: where Z and Z', which can be the same or different, indicate the side-chain groups of the amino acids commonly present in natural polypeptide molecules; c) using the reagent I,I-bis(trifluoroacetoxy)iodobenzene for the direct conversion of chain-terminal primary carboxyamide groups into amines; d) finally simultaneously releasing the entire peptide from the resin, the terminal NH 2 protector groups and the lateral functionalities compatible with the release conditions used.
Claim 3
Dependent Claim
167 words
The process as claimed in claim 1 for preparing the peptide: comprising: a) preparing the resin claimed under point 1, which by treatment with ethylenediamine is functionalised with primary amino groups at which the following have been condensed in succession: i) norleucine residues as internal standards; ii) the necessary "connection hooks" for condensing the C-terminal amino acid; b) condensing at the hydroxyl of the "connection hooks", methionine residues followed by leucine residues, with the amide functionalities blocked by N α -9-fluorenylmethoxycarbonyl groups; c) preparing the intermediate of general formula I, where Z is H and Z' is d) condensing the intermediate at the - groups of the leucine residues; e)- treating the peptide bonded to the resin, with I,I-bis(trifluoro- acetoxy)iodobenzene in a mixed aqueous-organic solvent; f) condensing, in succession, phenylalanine residues and pyroglutamic acid at the free amino ends obtained in stage 2e; and finally g) releasing the peptide chains from the resin by ammonolysis in methanol, followed by reduction of the methionine sulphoxide residues using N-methylmercaptoacetamide.
References Cited (Backward Citations)
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