Synthesis of Diverse N‐Substituted Muramyl Dipeptide Derivatives and Their Use in a Study of Human NOD2 Stimulation Activity. Issue 34 (16th July 2015)

• Record Type: Journal Article
• Authors: Chen, Kuo‐Ting; Huang, Duen‐Yi; Chiu, Cheng‐Hsin; Lin, Wan‐Wan; Liang, Pi‐Hui; Cheng, Wei‐Chieh
• Is Part Of: Chemistry. Volume 21:Issue 34(2015)
• Page Start: 11984
• Page End: 11988
• Publication Date: 2015-07-16
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201501557
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A flexible synthetic strategy toward the preparation of diverse <italic>N</italic>‐substituted muramyl dipeptides (<italic>N</italic>‐substituted MDPs) from different protected monosaccharides is described. The synthetic MDPs include <italic>N</italic>‐acetyl MDP and <italic>N</italic>‐glycolyl MDP, known NOD2 ligands, and this methodology allows for structural variation at six positions, including the muramic acid, peptide, and <italic>N</italic>‐substituted moieties. The capacity of these molecules to activate human NOD2 in the innate immune response was also investigated. It was found that addition of the methyl group at the <italic>C</italic>1 position of <italic>N</italic>‐glycolyl MDP significantly enhanced the NOD2 stimulating activity.</p> </abstract>