Chemoenzymatic Synthesis of New Aromatic Esters of Mono- and Oligosaccharides
Open Access
- 10 December 2020
- Vol. 8 (12), 1638
- https://doi.org/10.3390/pr8121638
Abstract
An efficient and convenient chemoenzymatic route for the synthesis of novel phenolic mono-, di- and oligosaccharide esters is described. Acetal derivatives of glucose, sucrose, lactose and inulin were obtained by chemical synthesis. The fully characterized pure sugar acetals were subjected to enzymatic esterification with 3-(4-hydroxyphenyl) propionic acid (HPPA) in the presence of Novozyme 435 lipase as a biocatalyst. The aromatic esters of alkyl glycosides and glucose acetal were obtained with good esterification yields, characterized by mass spectrometry (MALDI-TOF MS), infrared spectroscopy (FTIR) and nuclear magnetic resonance spectroscopy (1H NMR, 13C NMR). The synthesis of aromatic esters of disaccharide acetals was successful only for the enzymatic esterification of sucrose acetal. The new chemoenzymatic route allowed the synthesis of novel aromatic esters of inulin as the inulin monoacetal monoester and diester and the inulin diacetal monoester with a polymerization degree of two, as well as the inulin monoacetal monoester with a degree of polymerization of three, were obtained by enzymatic acylation of inulin acetals with HPPA. These compounds could represent a new class of sugar ester surfactants with enhanced bioactivity, antioxidative and antimicrobial properties and with potential application in drug delivery systems.This publication has 40 references indexed in Scilit:
- Microfluidic immobilized enzyme reactors for continuous biocatalysisReaction Chemistry & Engineering, 2019
- Enzymatic synthesis of short-chain flavor esters from natural sources using tailored magnetic biocatalystsFood Chemistry, 2019
- Novozym 435: the “perfect” lipase immobilized biocatalyst?Catalysis Science & Technology, 2019
- Driving Immobilized Lipases as Biocatalysts: 10 Years State of the Art and Future ProspectsIndustrial & Engineering Chemistry Research, 2019
- Profiling, characterization, and analysis of natural and synthetic acylsugars (sugar esters)Analytical Methods, 2017
- Advances in lipase-catalyzed esterification reactionsBiotechnology Advances, 2013
- Lipase mediated synthesis of sugar fatty acid estersProcess Biochemistry, 2011
- Lipase catalyzed ester synthesis for food processing industriesBrazilian Archives of Biology and Technology, 2009
- Enzyme‐catalyzed regioselective synthesis of sugar esters and related compoundsJournal of Chemical Technology & Biotechnology, 2006
- Enzymatic synthesis of hydrophilic and hydrophobic derivatives of natural phenolic acids in organic mediaJournal of Molecular Catalysis B: Enzymatic, 2001