Synthesis of N-[2-O-(2-Acetamido-1, 5-anhydro-2, 3-dideoxy-D-glucitol-3-yl)-D-lactoyl]-L-alanyl-D-isoglutamine (1-Deoxy-MDP) and Some of Its Lipophilic Analogs, and Their Immunoadjuvant Activities

Abstract

N-[2-O-(2-Acetamido-1, 5-anhydro-2, 3-dideoxy-D-glucitol-3-yl)-D-lactoyl]-L-alanyl-Disoglutamine (1-deoxy-MDP) and its lipophilic analogs were synthesized from 2-acetamido-3, 4, 6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride. The immunoadjuvant activity was examined in order to clarify the structural requirements of the carbohydrate moiety and the effects of the lipophilic character for this activity in N-acetylmuramoyl-L-alanyl-D-isoglutamine (MDP).