Total Synthesis of N-Acetylglucosamine-1,6-anhydro-N-acetylmuramylpentapeptide and Evaluation of Its Turnover by AmpD from Escherichia coli

• Published in: Journal of the American Chemical Society Vol. 131; no. 14; pp. 5187 - 5193
• Main Authors: Hesek, Dusan, Lee, Mijoon, Zhang, Weilie, Noll, Bruce C, Mobashery, Shahriar
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 15.04.2009; Amer Chemical Soc
• Subjects: Acetylglucosamine - analogs & derivatives; Acetylglucosamine - chemical synthesis; Acetylglucosamine - metabolism; Bacterial Proteins - metabolism; Cell Wall - metabolism; Chemistry; Chemistry, Multidisciplinary; Escherichia coli - enzymology; Glycosylation; Hydrolysis; Kinetics; N-Acetylmuramoyl-L-alanine Amidase - metabolism; Oligopeptides - chemical synthesis; Oligopeptides - metabolism; Physical Sciences; Science & Technology; Substrate Specificity; PEPTIDOGLYCAN FRAGMENTS; CELL-WALL; FACILE SYNTHESIS; TRACHEAL CYTOTOXIN; GLUCOSAMINE; LYTIC TRANSGLYCOSYLASE; CONVERGENT SYNTHESIS; SILYL MIGRATION; DERIVATIVES; MURAMYL PEPTIDES

The bacterial cell wall is recycled extensively during the course of cell growth. The first recycling event involves the catalytic action of the lytic transglycosylase enzymes, which produce an uncommon 1,6-anhydropyranose moiety during separation of the muramyl residues from the peptidoglycan, the...