87173-13-5Relevant academic research and scientific papers
Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments
Mashayekh, Siavash,Bersch, Klare L.,Ramsey, Jared,Harmon, Thomas,Prather, Benjamin,Genova, Lauren A.,Grimes, Catherine L.
, p. 16243 - 16253 (2021)
Peptidoglycan (PG) is the core structural motif of the bacterial cell wall. Fragments released from the PG serve as fundamental recognition elements for the immune system. The structure of the PG, however, encompasses a variety of chemical modifications among different bacterial species. Here, the applicability of organic synthetic methods to address this chemical diversity is explored, and the synthesis of cross-linked PG fragments, carrying biologically relevant amino acid modifications and peptide cross-linkages, is presented using solution and solid phase approaches.
A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction
Xing, Shuo,Gleason, James L.
, p. 1515 - 1520 (2015/01/30)
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.
