Synthesis of Novel 1,2,3-Triazolyl L-Serinol Palmitoyl Muramyl Dipeptide Derivatives

Abstract

In this research, a structural variant of muramyl dipeptide (MDP) is designed wherein, the entire N-acetyl group was replaced by a bio-isosteric 1,2,3-triazole moiety with serinol lipid substitution at 4th position. The protecting groups such as benzyl and benzylidine were removed sequentially to evolve three novel derivatives with increasing polarity as seen in the MDP-lipid 21-23 derivatives. A synthesis strategy involving triazolyl click chemistry to combine MDP scaffold to the serinol lipid head group is developed. The new derivatives were characterized using NMR, ESI-MS and MALDI. Preliminary data from in vitro screening of the compounds inferred the immuno-potentiating properties.