3554-93-6Relevant articles and documents
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.
supporting information, p. 16243 - 16253 (2020/11/13)
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.
Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases
DiFrancesco, Benjamin R.,Morrison, Zachary A.,Nitz, Mark
, p. 5631 - 5643 (2018/10/24)
The Carbohydrate Esterase family 4 contains virulence factors which modify peptidoglycan and biofilm-related exopolysaccharides. Despite the importance of this family of enzymes, a potent mechanism-based inhibition strategy has yet to emerge. Based on the postulated tridentate binding mode of the tetrahedral de-N-acetylation intermediate, GlcNAc derivatives bearing metal chelating groups at the 2 and 3 positions were synthesized. These scaffolds include 2-C phosphonate, 2-C sulfonamide, 2-thionoacetamide warheads as well as derivatives bearing thiol, amine and azide substitutions at the 3-position. The inhibitors were assayed against a representative peptidoglycan deacetylase, Pgda from Streptococcus pneumonia, and a representative biofilm-related exopolysaccharide deacetylase, PgaB from Escherichia coli. Of the inhibitors evaluated, the 3-thio derivatives showed weak to moderate inhibition of Pgda. The strongest inhibitor was benzyl 2,3-dideoxy-2-thionoacetamide-3-thio-β-D-glucoside, whose inhibitory potency showed an unexpected dependence on metal concentration and was found to have a partial mixed inhibition mode (Ki = 2.9 ± 0.6 μM).
Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives
Skarbek, Kornelia,Gabriel, Iwona,Szweda, Piotr,Wojciechowski, Marek,Khan, Muna A.,G?rke, Boris,Milewski, S?awomir,Milewska, Maria J.
, p. 79 - 87 (2017/06/20)
6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts