title: Chemical modification of the C-6 substituent in the carbohydrate moiety of N-acetylmuramoyl-L-alanyl-D-isoglutamine (MDP), and the immunoadjuvant activity.
abstract: N-Acetyl-6-O-mesyl-, -6-O-methyl-, and -4,6-di-O-methyl-muramoyl-L-alanyl-D-isoglutamine and N-acetyl-6-chloro-, -6-bromo-, and -6-azido-6-deoxymuramoyl-L-alanyl-D-isoglutamine were synthesized from benzyl 2-acetamido-2-deoxy-3-O-[D-1-(methoxycarbonyl) ethyl]-alpha-D-glucopyranoside and its 6-O-mesyl derivative. The immunoadjuvant activity of the products was examined, in order to clarify the structural requirements for the activity of the carbohydrate moiety in N-acetylmuramoyl-L-alanyl-D-isoglutamine.
mesh_terms: D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000031:analogs & derivatives*; D000276:Adjuvants, Immunologic; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D006168:Guinea Pigs; D006968:Hypersensitivity, Delayed; D013329:Structure-Activity Relationship
chemical_list: D000276:Adjuvants, Immunologic; D000119:Acetylmuramyl-Alanyl-Isoglutamine