Chemoenzymatic Synthesis of New Aromatic Esters of Mono- and Oligosaccharides
| Autor: | Marilena Motoc, Alina Ramona Buzatu, Anamaria Todea, Lambertus A.M. van den Broek, August E. Frissen, Carmen G. Boeriu |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Inulin
Disaccharide Bioengineering lcsh:Chemical technology 010402 general chemistry 01 natural sciences Chemical synthesis lcsh:Chemistry Acylation chemistry.chemical_compound BBP Sustainable Chemistry & Technology Chemical Engineering (miscellaneous) Organic chemistry lcsh:TP1-1185 Lipases VLAG chemistry.chemical_classification 010405 organic chemistry Chemistry Process Chemistry and Technology Acetal Nuclear magnetic resonance spectroscopy Oligosaccharide Sugar ester 0104 chemical sciences lcsh:QD1-999 Biocatalysis Aromatic oligosaccharides BBP Biorefinery & Sustainable Value Chains |
| Zdroj: | Processes, 8(12) Processes, Vol 8, Iss 1638, p 1638 (2020) Processes Volume 8 Issue 12 Processes 8 (2020) 12 |
| ISSN: | 2227-9717 |
| DOI: | 10.3390/pr8121638 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|