•Building trees of cellobiose and lactose are established.•The IR vibration signatures are agreeable to the experimental results.•Two conformers are first predicted here.•A tree-step computational approach can simplify the conformational determination.Great theoretical attentions have been paid on the conformational preference of individual molecular building blocks of carbohydrates because it is helpful for assignments of the experimental signals and explorations of the biological implications. A tree-step approach is applied here to simplify the conformational determination of phenyl β-cellobioside and benzyl β-lactoside, for which 35 and 23 initial structures are built, respectively. After the high-level calculations, low-energy conformers are determined and then compared with previous experimental and theoretical results. The low-energy conformers are reconstructed in our work for both cellobiose and lactose and the results show a quantitative agreement between the experimental signature and the predicted IR vibration assignment. In addition, two low-energy conformers, which are predicted in our work, have not been reported by the previous work using the traditional method. The tree-step computational approach provides an alternative timesaving and accurate method to focus on determining the preferred conformations of disaccharides.

The hydration structure of sodium glycinate (Na+GL−) is probed by the Monte-Carlo multiple minimum (MCMM) method combined with quantum mechanical (QM) calculations at the MP2/6-311++G(d,p) level. In the gas phase, the energy of [Na+GL−]β is more than 30 kJ mol−1 higher than [Na+GL−]α. With higher degrees of hydration, our results indicate that the most stable conformers of [Na+GL−]∙(H2O)8 were derived from [Na+GL−]β instead of [Na+GL−]α. The stable conformers determined by the conductor-like polarizable continuum model (CPCM) also show that [Na+GL−]β is more stable than [Na+GL−]α in the liquid phase. By analyzing the hydration process, water…water hydrogen bonding interaction will be more preferable than ion…water interaction as the number of water molecules increases. According to the electronic density at the bond critical point on the Na-X bonds (X = O1, O2, N) in the low-energy conformers, Na+GL− will be dissociated as Na+ and GL− in the bulk water, which is not predicted by the CPCM model. The structure features and the charge redistribution of Na+GL− will provide a physical explanation for the weakening Na-O1 interaction.

A tree-step computational approach has been applied to determine the lowest-energy conformers of luteolin-4′-O-β-D-glucoside (L4′G). Fifty-seven starting structures of the L4′G have been built, and then by performing with density functional theory (DFT) optimizations and second-order Møller-Plesset (MP2) calculations, the preferred conformations of L4′G are predicted. In order to test the accuracy of the computational approach, a hybrid Monte-Carlo multiple minimum (MCMM)/quantum mechanical (QM) approach is applied to determine the favorable conformers of L4′G. The alternative classification is employed to put similar conformations into the same catalogue according to the dihedral angles among the luteolin rings, glycosidic dihedral angles, and the orientations of hydroxyl and hydroxymethyl groups. The low-energy conformations are located after the optimizations at the HF/6-31G(d) and B3LYP/6-311+G(d) levels. Compared with the hybrid MCMM/QM approach, the tree-step computational approach not only remains accurate but also saves a lot of computing resources.