title: Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium.
abstract: In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium . 6-Amino-6-deoxy-alpha-D-methylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and beta-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 x 10(-4) mol mL(-1), it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, (1)H NMR, and (13)C NMR spectroscopy.
authors.affiliation: UMR US2B, Unité des Sciences du Bois et des Biopolymères, Université Bordeaux 1, INRA, CNRS, Talence, France.
authors.forename: Théoneste
authors.initials: T
authors.lastname: Muhizi
authors.forename: Stéphane
authors.initials: S
authors.lastname: Grelier
authors.forename: Véronique
authors.initials: V
authors.lastname: Coma
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D055598:Chemical Phenomena; D003847:Deoxyglucose / Q000031:analogs & derivatives*; D005944:Glucosamine / Q000138:chemical synthesis / Q000494:pharmacology; D008087:Listeria / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D012486:Salmonella typhimurium / Q000187:drug effects*; D017550:Spectroscopy, Fourier Transform Infrared; D013329:Structure-Activity Relationship
chemical_list: D000900:Anti-Bacterial Agents; C014968:kanosamine; D003847:Deoxyglucose; D005944:Glucosamine