Synthesis of peptide and glycopeptide fragments of bacterial cell walls

Abstract

Peptides, ranging from tetrapeptide I, II to octadecapeptide XXI and from N-acetylmuramyl-hexapeptide XXIII to tris(N-acetylmuramyl)-octadecapeptide XXVII, were prepared using synthesis in solution as well as solid-phase synthesis. H-L-Ala-D-iGln-L-Lys-D-Ala-(L-Ala)2-OMe (VIII) and its lysine-acetylated analogue X were pyrogenic and the former (VIII) exhibited weak immunoadjuvant activity. The immunoadjuvant activity of tris(N-acetylmuramyl)-octadecapeptide XXVII was comparable with that of MDP and the compound was not pyrogenic.