Collect. Czech. Chem. Commun. 1987, 52, 1609-1624

Synthesis of peptide and glycopeptide fragments of bacterial cell walls

Jan Ježeka, Radovan Strakab, Viktor Krchňákc, Miloš Rybaa, Jiří Rottab, Peter Mayerd and Milan Zaorala

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia
b Institute of Hygiene and Epidemiology, 100 42 Prague 10, Czechoslovakia
c Léčiva-Pharmaceuticals, 140 00 Prague 4, Czechoslovakia
d SANDOZ Forschungsinstitut G.m.b.H., Brunnerstrasse 59, A 1235 Wien, Österreich


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.