Synthesis and Antibacterial Activity of Aminodeoxyglucose Derivatives against Listeria innocua and Salmonella typhimurium

Theoneste Muhizi (1) , Stéphane Grelier (2, 3) , Véronique Coma (2, 3)

1 Us2b - Unité des Sciences du bois et des biopolymères
2 LCPO - Laboratoire de Chimie des Polymères Organiques
3 Team 2 LCPO : Biopolymers & Bio-sourced Polymers

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.

Mots clés: Antibacterial activity; aminodeoxyglucoses; Salmonella typhimurium; Listeria innocua

Domaines: Polymères

Theoneste Muhizi, Stéphane Grelier, Véronique Coma. Synthesis and Antibacterial Activity of Aminodeoxyglucose Derivatives against Listeria innocua and Salmonella typhimurium. Journal of Agricultural and Food Chemistry, 2009, 57 (19), pp.8770-8775. ⟨10.1021/jf901609y⟩. ⟨hal-00944893⟩