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.

Alkyl-imidazolium glycosides: non-ionic—cationic hybrid surfactants from renewable resources

“…salts of oxidized glycosides with a carboxylic acid, 17e19 on the one hand, and cationic N-alkylated amino-derivatives of sugars on the other. Chemical instability 20,21 limits the application of glycosylamines 22 and their subsequent ammonium ions, 23 which resemble the potentially most easily accessible sugar based cationic surfactants.…”

Synthesis and X-ray crystallographic investigation of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)alkanamides as analogs of N-glycoprotein linkage region

“…The reported literature procedure [9] was employed for converting 1,2:5,6-di-O-isopropylidene-α-Dglucofuranose to the C3 azido sugar (5) (Scheme 1). Reduction of 5 using Pd/C under hydrogen atmosphere followed by N-acetylation of the resultant amine using acetic anhydride/pyridine gave the C3 acetamide (6).…”

“…Synthesis of 1,2:5,6-di-O-isopropylidene-3-deoxy-3-acetamido-α-D-glucofuranose (6) 1,2,5,6-Di-O-isopropylidene-3-deoxy-3-azido-α-D-glucofuranose (5) [9] (0.7 g, 2.46 mmol) and Pd/C (70 mg) were taken in CH 2 Cl 2 (3 mL) and the mixture was stirred at 30°C under H 2 atmosphere for 3 h. Pyridine (0.79 mL) and acetic anhydride (0.46 mL, 4.92 mmol) were then added at 0°C and stirring was continued overnight. The mixture was filtered through celite and washed with MeOH.…”

Polysaccharide-based Biomaterials with Antimicrobial and Antioxidant Properties

“…A very interesting review summarizes the chitosan MIC values according to recent data found in the literature [68] , indicating that the effectiveness of this aminopolysaccharide is dependent on microbial species. Our group has been published several papers dealing with the bioactive properties of chitosan-based matrices [69][70][71][72] and with the bioactivity of glucosamine derivatives [73][74][75] .…”