Process for the preparation of retro-inverso peptides and new in

Chemistry: natural resins or derivatives; peptides or proteins; – Peptides of 3 to 100 amino acid residues – Peptides with at least one nonpeptide bond other than a...

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530330, 530334, 530337, 530338, 930 31, C07K 108, C07K 502, C07K 702

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active

051169479

ABSTRACT:
A method of synthesis of a partially retro-inverso peptide incorporating at least one malonyl residue of formula (III) ##STR1## wherein R represents the side chain of an .alpha.-amino acid, is described which is characterized in that said malonyl residue is incorporated by condensing a 5-substituted-2,2-dimethyl-1,3-dioxane-4,6-dione of formula (IV) ##STR2## wherein R' is the side-chain R wherein the functional groups, if any, are suitably protected, with an amino acid, amino acid amide, peptide fragment, or pseudo-peptide fragment wherein the terminal carboxyl group, if present, and the possible side-chain functionalities are suitably protected and the reactive amino group is tri-alkyl-silylated.
The new compounds of formula (VI) and a process for the preparation of a partially retro-inverso tuftsin analog which involves use of said method and said intermediate are also described and claimed.

REFERENCES:
patent: 4816560 (1989-03-01), Verdini et al.
patent: 5061811 (1991-10-01), Pinori et al.
Chemical Abstracts, vol. 86:105,604d (1977).
Chemical Abstracts, vol. 108:75,313m (1988).

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