title: Synthesis of Diverse N-Substituted Muramyl Dipeptide Derivatives and Their Use in a Study of Human NOD2 Stimulation Activity.
abstract: A flexible synthetic strategy toward the preparation of diverse N-substituted muramyl dipeptides (N-substituted MDPs) from different protected monosaccharides is described. The synthetic MDPs include N-acetyl MDP and N-glycolyl MDP, known NOD2 ligands, and this methodology allows for structural variation at six positions, including the muramic acid, peptide, and N-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 C1 position of N-glycolyl MDP significantly enhanced the NOD2 stimulating activity.
authors.affiliation: Genomics Research Center, Academia Sinica No. 128, Academia Road Sec. 2, Nankang District, Taipei, 115 (Taiwan).|School of Pharmacy, National Taiwan University, No. 17, Xuzhou Road, Taipei 100 (Taiwan).
authors.forename: Kuo-Ting
authors.initials: KT
authors.lastname: Chen
authors.affiliation: Department of Pharmacology, National Taiwan University, No. 1, Jen-Ai Road, Sec. 1, Taipei 100 (Taiwan).
authors.forename: Duen-Yi
authors.initials: DY
authors.lastname: Huang
authors.affiliation: Genomics Research Center, Academia Sinica No. 128, Academia Road Sec. 2, Nankang District, Taipei, 115 (Taiwan).
authors.forename: Cheng-Hsin
authors.initials: CH
authors.lastname: Chiu
authors.affiliation: Department of Pharmacology, National Taiwan University, No. 1, Jen-Ai Road, Sec. 1, Taipei 100 (Taiwan). wwllaura1119@ntu.edu.tw.
authors.forename: Wan-Wan
authors.initials: WW
authors.lastname: Lin
authors.affiliation: School of Pharmacy, National Taiwan University, No. 17, Xuzhou Road, Taipei 100 (Taiwan). phliang@ntu.edu.tw.
authors.forename: Pi-Hui
authors.initials: PH
authors.lastname: Liang
authors.affiliation: Genomics Research Center, Academia Sinica No. 128, Academia Road Sec. 2, Nankang District, Taipei, 115 (Taiwan). wcheng@gate.sinica.edu.tw.
authors.forename: Wei-Chieh
authors.initials: WC
authors.lastname: Cheng
mesh_terms: D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000138:chemical synthesis* / Q000737:chemistry; D006801:Humans; D007113:Immunity, Innate / Q000187:drug effects*; D008024:Ligands; D015394:Molecular Structure
chemical_list: D008024:Ligands; D000119:Acetylmuramyl-Alanyl-Isoglutamine
keywords: N-substituted muramyl dipeptide; NOD2; bioorganic chemistry; peptides; synthetic methods