Surface activities, biodegradability and antimicrobial properties of glucosamine derivatives containing alkyl chains

Abstract

Three series of D‐glucosamine derivatives containing an alkyl chain with 8 to 14 atoms, methyl 2‐acylamino‐2‐deoxy‐D‐glucopyranosides, n ‐alkyl 2‐acetylamino‐2‐deoxy‐D‐glucopyranosides and n ‐alkyl 2‐amino‐2‐deoxy‐D‐glucopyranoside hydrochlorides, were synthesized, and their surface properties (such as surface tension, critical micelle concentration (CMC), dynamic surface tension and foaming properties), biodegradability and antimicrobial activities were evaluated. n ‐Alkyl 2‐amino‐2‐deoxy‐D‐glucopyranoside hydrochlorides containing C8 to C12 carbon chains showed surface activities, a CMC and excellent foaming properties. The α‐anomers showed a slightly lower CMC than the β‐anomers, indicating less hydrophilicity of the α‐anomers. On the other hand, glucosamine derivatives containing amide groups showed poor surface activities in water due to their lower solubilities in water. All glucosamine derivatives containing alkyl chains were biodegraded as well as conventional ethoxylated nonionics by activated sludge from the municipal sewage treatment plant. Methyl 2‐acylamino‐2‐deoxy‐D‐glucopyranosides and n ‐alkyl 2‐amino‐2‐deoxy‐D‐glucopyranoside hydrochlorides showed a broader spectrum of antimicrobial activity than the corresponding n ‐alkyl glucopyranosides. Among them the C12 derivatives showed the best results.