title: A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction.
abstract: A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible SN2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke St. West, Montreal, Quebec, Canada H3A 0B8. jim.gleason@mcgill.ca.
authors.forename: Shuo
authors.initials: S
authors.lastname: Xing
authors.forename: James L
authors.initials: JL
authors.lastname: Gleason
mesh_terms: D000119:Acetylmuramyl-Alanyl-Isoglutamine / Q000138:chemical synthesis* / Q000737:chemistry*; D000478:Alkylation; D001386:Azides / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D010084:Oxidation-Reduction
chemical_list: D001386:Azides; D000119:Acetylmuramyl-Alanyl-Isoglutamine