Process for the preparation of retro-inverso peptides and...

C - Chemistry – Metallurgy – 07 – K

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530/7.06, 260/35

C07K 5/033 (2006.01) C07D 319/06 (2006.01) C07K 1/02 (2006.01) C07K 1/04 (2006.01) C07K 5/02 (2006.01)

Patent

CA 2006560

CASE 2977 1. PROCESS FOR THE PREPARATION OF RETRO-INVERSO PEPTIDES AND NEW INTERMEDIATES THEREOF Abstract A method of synthesis of a partially retro-inverso peptide incorporating at least one malonyl residue of formula (III) Image (III) 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 (VI) Image ( VI ) wherein R' is the side-chain R wherein the functional groups, if any, are suitably protected, with an amino 2. 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.

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