posted on 2021-10-04, 15:15authored byMichael A. Jackson, Kervin O. Evans, Neil P. J. Price, Judith A. Blackburn, Charles J. Ward, Karen J. Ray, Karl E. Vermillion
β-C-Glycoside ketone derivatives of glucose,
lactose, and maltose were converted to amines via a reductive amination
using 5 wt % Rh/Al2O3 in ammoniacal methanol
under 34 bar H2. The amines were isolated and then were
used as the amine in the reductive amination of 2-undecanone that
can be prepared from the seed oil of Cuphea. The
resulting β-C-glycoside-2-aminoundecanes were
characterized by MALDI-TOF mass spectrometry and 2D NMR. The critical
micelle concentrations of the products as measured by isothermal calorimetry
titration ranged from 1 to 5 mM, and the micelles carry a positive
charge as measured by zeta potentials. The β-C-glycoside 2-aminoundecanes have antimicrobial activity against Bacillus subtilis, Pseudomonas aeruginosa, Erwinia amylovora, and Escherichia coli, with the C-glucoside
derivative having the greatest activity with a minimum inhibitory
concentration of 0.31 mM and a minimum bactericide concentration of
0.62 mM against the Gram positive organisms. Against the Gram negative Erwinia and Escherichia, the MIC is 0.62 mM. This work introduces a new family of sustainable
surfactants with potential uses in personal care and cleaning products.