Probing n-Octyl α-d-Glycosides Using Deuterated Water in the Lyotropic Phase by Deuterium NMR

The lyotropic phase behavior of four common and easily accessible glycosides, n-octyl α-d-glycosides, namely, α-Glc-OC₈, α-Man-OC₈, α-Gal-OC₈, and α-Xyl-OC₈, was investigated. The presence of normal hexagonal (H_I), bicontinuous cubic (V_I), and lamellar (L_α) phases in α-Glc-OC₈ and α-Man-OC₈ including their phase diagrams in water reported previously was verified by deuterium nuclear magnetic resonance (²H NMR), via monitoring the D₂O spectra. Additionally, the partial binary phase diagrams and the liquid crystal structures formed by α-Gal-OC₈ and α-Xyl-OC₈ in D₂O were constructed and confirmed using small- and wide-angle X-ray scattering and ²H NMR. The average number of bound water molecules (n_b) per headgroup in the L_α phase was determined by the systematic measurement of the quadrupolar splitting of D₂O over a wide range of molar ratio values (glycoside/D₂O), especially at high glucoside composition. The number of bound water molecules bound to the headgroup was found to be around 1.5-2.0 for glucoside, mannoside, and galactoside, all of which possesses four OH groups. In the case of xyloside, which has only three OH groups, the bound water content is ∼2.0. Our findings confirmed that the bound water content of all n-octyl α-d-glycosides studied is lower compared to the number of possible hydrogen bonding sites possibly due to the fact that most of the OH groups are involved in intralayer interaction that holds the lipid assembly together.