In vitro and in silico study on glucosylation of caprylyl glycol

Abstract Caprylyl glycol is commonly used in the cosmetic industry due to its good antimicrobial and skin-dehydrating properties. It has numerous applications in the pharmaceutical industry in drug formulations. However, its utility is diminished due to its insoluble nature which restricts its applicability in various cosmetic formulations and industrial products. This study introduces a cost-effective method for glycosylating caprylyl glycol by using sucrose as an inexpensive alternative to uridine diphosphate glucose (UDP-glucose) catalyzed by Deinococcus geothermalis amylosucrase (DgAS). This system offers numerous advantages including swiftness, directness of product formation from the substrate, efficacy, thermal stability, and regiostability in vitro at 40 °C. This study demonstrated an impressive conversion of approximately 95% in vitro and produced a novel caprylyl glycol 2- O -glucoside, which HPLC, NMR, and mass spectrometry characterized. Molecular docking of DgAS with caprylyl glycol and its glycoside supported the proposed mechanism for enzymatic synthesis of caprylyl glycol 2- O -glucoside in vitro. Furthermore, density functional theory-based analysis also precluded the acidic nature of the secondary hydroxyl group (susceptible nucleophilic center) of caprylyl glycol where glucosylation was confirmed. The outcomes of this work will be beneficial for synthesizing similar glycosides for industrial applications.