Collect. Czech. Chem. Commun.
1982, 47, 2989-2995
https://doi.org/10.1135/cccc19822989
Preparation and some biological properties of N-acetylmuramyl-alanyl-D-isoglutamine (MDP) analogues
Milan Zaorala, Jan Ježeka and Jiří Rottab
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
The condensation of 1-α-O-benzyl-4,6-O-benzylidene-N-acetylgalactomuramic acid (I), 1-α-O-benzyl-4,6-O-benzylidene-N-acetylallomuramic acid (VIII), and 1-α-O-benzyl-4,6-O-benzylidene-N-acetylnorallomuramic acid (XI) with alanyl-D-isoglutamine benzyl ester afforded 1-α-O-benzyl-4,6-O-benzylidene-N-acetylgalactomuramyl-alanyl-D-isoglutamine benzyl ester (XII), 1-α-O-benzyl-4,6-O-benzylidene-N-acetylallomuramyl-alanyl-D-isoglutamine benzyl ester (XIII) and 1-α-O-benzyl-4,6-O-benzylidene-N-acetylnorallomuramyl-alanyl-D-isoglutamine benzyl ester (XIV). Protecting groups were removed from XII-XIV and N-acetylgalactomuramyl-alanyl-D-isoglutamine (XV), N-acetylallomuramyl-alanyl-D-isoglutamine (XVI), and N-acetylnorallomuramyl-alanyl-D-isoglutamine (XVII) were obtained. XV-XVII showed lower pyrogenic and immunoadjuvant effect than N-acetylmuramyl-alanyl-D-isoglutamine.
