Synthesis of carbohydrate analogs (positional, configurational, and optical) of n-acetylmuramoyl-L-alanyl-D-isoglutamine, and their immunoadjuvant activities.
2-Acetamido-2-deoxy-4- and -6-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose, 2-acetamido-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-allopyranose,  -D-gulopyranose, -D-galactopyranose, -D-mannopyranose, and -L-idopyranose, and 3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D- and -L-glucopyranose were synthesized, in order to clarify the structural requirements for the immunoadjuvant activity of the carbohydrate moiety in N-acetylmuramoyl-L-alanyl-D-isoglutamine. Immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea-pigs.
D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D000276:Adjuvants, Immunologic / Q000138:chemical synthesis*; D000818:Animals; D006020:Glycopeptides / Q000138:chemical synthesis*; D006168:Guinea Pigs; D007536:Isomerism; D008722:Methods; D012882:Skin Tests; D013329:Structure-Activity Relationship
D000276:Adjuvants, Immunologic; D006020:Glycopeptides; D000119:Acetylmuramyl-Alanyl-Isoglutamine