Chemoenzymatic synthesis of new aromatic esters of mono-and oligosaccharides

Alina Ramona Buzatu, August E. Frissen, Lambertus A.M. van den Broek, Anamaria Todea*, Marilena Motoc, Carmen Gabriela Boeriu

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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.

Original languageEnglish
Article number1638
JournalProcesses
Volume8
Issue number12
DOIs
Publication statusPublished - 11 Dec 2020

Keywords

  • Aromatic oligosaccharides
  • Lipases
  • Sugar ester

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