45159-25-9Relevant articles and documents
Ten-membered rings as key interaction motifs in folding of desmuramyl di-, tri-, and tetrapeptides
Ribi?, Rosana,Kodrin, Ivan,Biljan, Ivana,Paurevi?, Marija,Tomi?, Sr?anka
, p. 743 - 754 (2019)
Muropeptides are fragments of polymeric peptidoglycan, unique constituent of bacterial cell walls, acting as immunostimulators (adjuvants). The smallest biologically active unit of peptidoglycan is N-acetylmuramyl-L-alanyl-D-isoglutamine. In this paper, the synthesis and conformational analysis of desmuramyl peptides, derivatives lacking the N-acetylmuramyl moiety, is described. Systematic conformational analysis (bottom-up approach) of peptides in zwitterionic and non-zwitterionic forms of corresponding desmuramyl di-, tri-, and tetrapeptides was performed and results were compared with experimental data obtained by NMR study. Ten-membered ring (C10, N1bH?O3) formed between isoGln amide group and C=O of AdGly was found to be a key interaction that constitutes the central structural spine and initiates β-turn-like folding in our model peptide systems.
Synthesis of muramyl dipeptide analogs with enhanced adjuvant activity
Kobayashi,Fukuda,Yukimasa,et al.
, p. 2570 - 2577 (2007/10/02)
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