Process for the preparation of retro-inverso peptides and 1,3-dioxane-4,6-dione intermediates thereof

US5061811A · kind A · utility

Assignee

• Sclavo SpA · IT

Inventors

• Massimo Pinori · Paderno d'Adda, IT
• Felice Centini · Roma, IT
• Antonio S. Verdini · Monterotondo, IT

Key dates

• Filing date: Dec 14, 1989
• Grant date: Oct 29, 1991
• Expiry date: Dec 14, 2009

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07K5/0212
• WIPO field: Biotechnology
• WIPO sector: Chemistry

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 (VI) ##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 fagment 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.