Synthesis of a Biologically Active Fluorescent Muramyl Dipeptide Congener

Article abstract of DOI:10.1021/jm00366a014

A fluorescent-labeled muramyl dipeptide (MDP) has been prepared to probe immunoadjuvant cellular interactions.N-Acetylmuramyl-L-alanyl-D-isoglutamine (1) was synthesized in improved yield and reacted with 2-(fluoroesceinylamino)-4,6-dichloro-s-triazine (DTAF,2) to give the fluorescent adduct DTAF-MDP (3), attached through the 6-position of the sugar moiety.Adjuvant activity was assessed by using two different in vitro assays, macrophage spreading, and inhibition of macrophage migration.Both assays indicated that the apparent adjuvant activity of 3 is comparable to that of 1.