Collect. Czech. Chem. Commun.
1980, 45, 1424-1446
https://doi.org/10.1135/cccc19801424
Synthesis of peptides, glyco derivatives and glycopeptides from bacterial cell walls
Milan Zaorala, Jan Ježeka, Viktor Krchňáka and Radovan Strakab
a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Institute of Hygiene and Epidemiology, 100 42 Prague 10
Abstract
Syntheisi in solution and in solid phase was used to prepare alanyl-D-isoglutamine (VI), alanyl-D-isoglutaminyl-Nε-p-toluenesulfonyl-lysyl-D-alanine ester (XIII), alanyl-D-isoglutaminyl-Nε-acetyl-lysyl-D-alanine methyl ester (XIV), alanyl-D-isoglutaminyl-Nε-acetyl-lysyl-D-alanyl-pentaglycine methyl ester and amide (XXXI, XXXII), alanyl-D-isoglutaminyl-Nε-acetyl-lysyl-D-alanyl-pentaglycyl------------- alanyl-D-isoglutaminyl-lysyl-D-alanine methl ester (XXXV), alanyl-D-isoglutaminyl-Nε-acetyl-lysyl-D-alanyl-pentaalanyl-----------------alanyl-D-isoglutaminyl-lysyl-D-alanine methyl ester (XXXVII), N-acetylmuramyl-alanyl-D-isoglutaminyl-Nε-acetyl-lysyl-D-alanyl-pentaglycine amide (XXXIX), N-acetylmuramyl-alanyl-E-isoglutaminyl-Nε-acetyl-lysyl-D-alanyl-pentaglycyl------------------------ alanyl-D-isoglutaminyl-lysyl-D-alanine methyl ester (XLI), and N-acetylmuramyl-alanyl-D-isoglutaminyl-Nε-acetyl-lysyl-pentaalanyl-----------------------------N-acetylmuramyl-alanyl-D-isoglutaminyl-lysyl-D-alanine methyl ester (XLIII). The tetrapeptides, nanopeptides, and tridecapeptides show a pronounced pyrogenic effect. Immunoadjuvant activity was observed not only with the glycopeptides but also with nonapeptide XXXI.
