An Original Strategy for Gln Containing Peptide Synthesis Using SPPS and Glu(OH)-1-OAll

Using multiple peptide synthesis in parallel, a series of 24 compounds analogues of tripeptide sequence Z-Leu-Phe-Gln-H, modified by imidazole moiety were synthesized. An effective and simple scheme for including imidazole heterocycle to C- and/or N-terminus of Gln residue was created by means of allyl group as α-COOH protecting group for Fmoc-Glu. The approach using Fmoc-Glu-1-OAll as a first amino acid linked to the resin could be useful for the synthesis of a large number of amino acids and/or heterocyclic moieties including compounds. Based on the preliminary biological trials we could conclude that the presence of imidazole heterocycle affect positively the antiviral activity against Coxsackieviruses B1 and Poliovirus type 1.