Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• muramyl peptides induce significantly higher activation of NOD2 than MDP [29][30]. Mycobacteria present in complete Freund’s adjuvant, and related Actinomycetes, produce N-glycolyl MDP by the hydroxylase action on MDP (N-acetylmuramic acid within the peptidoglycan). The influence of structural

An efficient synthesis of 1,6-anhydro-N-acetylmuramic acid from N-acetylglucosamine

• Matthew B. Calvert,
• Christoph Mayer and
• Alexander Titz

Beilstein J. Org. Chem. 2017, 13, 2631–2636, doi:10.3762/bjoc.13.261

• Microbiology and Infection Medicine Tübingen (IMIT), Department of Microbiology and Biotechnology, University of Tübingen, Germany Department of Pharmacy, Saarland University, Saarbrücken, Germany 10.3762/bjoc.13.261 Abstract A novel synthesis of 1,6-anhydro-N-acetylmuramic acid is described, which proceeds

• in only five steps from the cheap starting material N-acetylglucosamine. This efficient synthesis should enable future studies into the importance of 1,6-anhydromuramic acid in bacterial cell wall recycling processes. Keywords: N-acetylmuramic acid; anhydrosugars; antibiotic resistance; bacterial

• cell wall recycling; carbohydrate synthesis; Introduction 1,6-Anhydro-N-acetylmuramic acid (AnhydroMurNAc, 1, Figure 1) and its derivatives (e.g., 2 and 3) are of great interest due to their integral role in bacterial cell wall recycling [1][2] and the induction of antibacterial resistance [3

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• : Bacterial cell walls consist of peptidoglycan, a heteropolymer with long chains of alternating units of N-acetylmuramic acid (MurNAc) and N-acetylglucosamine (GlcNAc) that are cross-linked through peptide chains attached to the muramic acid sugar (Figure 3) [52]. The biosynthesis of peptidoglycan is

Design, automated synthesis and immunological evaluation of NOD2-ligand–antigen conjugates

• Marian M. J. H. P. Willems,
• Gijs G. Zom,
• Nico Meeuwenoord,
• Ferry A. Ossendorp,
• Herman S. Overkleeft,
• Gijsbert A. van der Marel,
• Jeroen D. C. Codée and
• Dmitri V. Filippov

Beilstein J. Org. Chem. 2014, 10, 1445–1453, doi:10.3762/bjoc.10.148

• -acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc) of which the lactic acid is connected to a peptide [24]. Where NOD1 recognizes diaminopimelic acid containing peptides [25][26], the minimal structural element of PG required for activation of the intracellular protein NOD2 is N-acetylmuramyl-L-alanine-D