Biocatalytic approach to the chemoselective acylation of sesquiterpene lactones from chicory: a pathway to novel ester derivatives

19 June 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

In this study, we explore the use of the immobilized lipase Novozym 435 in the selective acylation of chicory sesquiterpene lactones (STLs) - lactucin (Lc), 11β,13-dihydrolactucin (DHLc), lactucopicrin (Lp), and 11β,13-dihydrolactucopicrin (DHLp) - using aliphatic vinyl esters as acyl donors. Despite the scarcity of these STLs due to their challenging extraction process and high cost, our results demonstrate the broad applicability and very high efficiency of this method. Furthermore, this methodology enables the selective esterification of the primary alcohol group without transesterifying the existing ester in the substrates. We also describe the enzyme-substrate binding modes in the acylation reactions with STLs, as well as the nature of their interactions with crucial amino acid residues at the active site, providing further insight into the potential of this approach. This study forms a foundation for the tailored functionalization of STLs, offering possibilities for the synthesis of STL derivatives with significant potential applications as pharmaceuticals or biocontrol agents.

Keywords

Biocatalysis
Sesquiterpene Lactones
Lipase
Novozym435
Chicory
Terpene

Supplementary materials

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Supplemental Information
Description
Contains chromatograms (GC-FID and LC-MS), NMR (proton, carbon, HSQC) and mass (Qtof) spectra of the main compounds related to the lipase-catalyzed acylation reactions described in the article; as well as a scheme of the reaction used to synthesize aromatic vinyl esters used as acyl donors.
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Comment number 1, Juan RODRIGUEZ MOSHEIM: Jun 21, 2023, 15:30

Version #2 with some minor corrections will be made available shortly !