Beilstein J. Org. Chem.2014,10, 1445–1453, doi:10.3762/bjoc.10.148
incorporated antigen. Here we describe the design, automated synthesis and immunological evaluation of a set of four muramyl dipeptide–peptide antigen conjugates. Muramyl dipeptide (MDP) represents a well-known ligand for the intracellular NOD2receptor and our study shows that covalently linking an MDP-moiety
to an antigenic peptide can lead to a construct that is capable of stimulating the NOD2receptor if the ligand is attached at the anomeric center of the muramic acid. The constructs can be processed by dendritic cells (DCs) and the conjugation does not adversely affect the presentation of the
incorporated SIINFEKL epitope on MHC-I molecules. However, stimulation of the NOD2receptor in DCs was not sufficient to provide a strong immunostimulatory signal.
Keywords: automated synthesis; glycopeptide; innate immunity; muramyl dipeptide; NOD2receptor; solid phase synthesis; Introduction
In recent