Molecular docking and density functional theory calculations of vinpocetine and teicoplanin aglycone chiral selector

Abstract

Chiral separation has been an essential issue as stereochemistry significantly influences the biological activity. In some cases, one stereoisomer may show effectiveness in pharmacology activities while the other may appear toxic. Thus, devising technology with knowledge at the fundamental level becomes crucial in the field of chiral separation. This work presented molecular docking simulation and quantum chemical calculation of vinpocetine (VP) drug stereoisomers complexation with teicoplanin aglycone (TAG) chiral selector. Docking simulation was used to find the best conformation of VP stereoisomers with TAG chiral selector followed by density functional theory (DFT) calculation at B3LYP-D3(BJ)/6–31 g(d) level of theory representing the second phase of this work. The stability of VP–TAG inclusion complexes based on binding energy differences obtained from the quantum-chemical calculation was in the order of (3R16S)VP–TAG > (3R16R)VP–TAG > (3S16S)VP–TAG > (3R16S)VP–TAG. The significant differences in the binding energy suggested that the chiral separation of VP stereoisomers can be achieved using TAG.