Immobilized Fe3O4-Polydopamine-Thermomyces lanuginosus Lipase-Catalyzed Acylation of Flavonoid Glycosides and Their Analogs: An Improved Insight Into Enzymic Substrate Recognition.

Zhaoyu Wang,Mingyi Li,Yang Li,Si Luo,Xiaohui Zhang,Qingxia Ji,Yanhong Bi,Xiaojuan Zhao

doi:10.3389/fbioe.2021.798594

Abstract

The conversion of flavonoid glycosides and their analogs to their lipophilic ester derivatives was developed by nanobiocatalysts from immobilizing Thermomyces lanuginosus lipase (TLL) on polydopamine-functionalized magnetic Fe3O4 nanoparticles (Fe3O4-PDA-TLL). The behavior investigation revealed that Fe3O4-PDA-TLL exhibits a preference for long chain length fatty acids (i.e., C10 to C14) with higher reaction rates of 12.6–13.9 mM/h. Regarding the substrate specificity, Fe3O4-PDA-TLL showed good substrate spectrum and favorably functionalized the primary OH groups, suggesting that the steric hindrances impeded the secondary or phenolic hydroxyl groups of substrates into the bonding site of the active region of TLL to afford the product.

Highlights

Ever since the groundbreaking work of Klibanov in the early 1980s (Zaks and Klibanov, 1984), nonaqueous enzymology has represented a significant extension of organic synthetic processes that come with more challenges—or that is even impossible—compared with traditional chemical approaches (Hughes and Lewis, 2018; van Schie et al, 2021)
Comparative experiments were initially devoted to an enzyme screening based on the decanoylation of polydatin as a model reaction
Thermomyces lanuginosus lipase (TLL) immobilized on magnetic Fe3O4-PDA makes the isolation of product very easy as the catalyst can be removed from the reaction with the help of a magnet

Summary

Introduction

Ever since the groundbreaking work of Klibanov in the early 1980s (Zaks and Klibanov, 1984), nonaqueous enzymology has represented a significant extension of organic synthetic processes that come with more challenges—or that is even impossible—compared with traditional chemical approaches (Hughes and Lewis, 2018; van Schie et al, 2021). Studies over the past 30 years have revealed that enzymatic catalysis shows unusual abilities and can be a powerful tool for synthesizing fine chemicals in the pharmaceutical, food, and cosmetic industries (Sheldon and Pereira, 2017; SÁ et al, 2017). Flavonoid glycosides and their analogs are a large group of well-known natural plant secondary metabolites that are of great academic and industrial interest because of their potentially beneficial biological, pharmacological, and medicinal properties (Chen et al, 2018; Yang et al, 2018).

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Conclusion