Synthesis and antimicrobial properties of amphiphilic sugar derivatives containing sulfur and nitrogen

Two series of methyl α-D-glucoside derivatives containing an alkyl chain with 8 to 16 atoms, methyl 6-N-alkylamino-6-deoxy-α-D-glucoside and methyl 6-alkylthio-6-deoxy-α-D-glucoside, were synthesized and their antimicrobial activities were evaluated. All of the compounds tested were found to show inhibitory activities, and these activities were dependent on alkyl chain length. In particular, methyl α-D-glucoside derivatives with a dodecyl group showed considerable inhibitory activity. Among the dodecyl derivatives, the sulfur derivative was more effective than the imino derivative.