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Green synthesis of (R)-3-hydroxy-decanoic acid and analogs from levoglucosenone: a novel access to the fatty acid moiety of rhamnolipids

Authors :
Enzo Petracco
Amandine L. Flourat
Marie-Charlotte Belhomme
Stéphanie Castex
Fanny Brunissen
Fanny Brunois
Aurélien A. M. Peru
Florent Allais
Arnaud Haudrechy
Source :
Frontiers in Chemistry, Vol 12 (2024)
Publication Year :
2024
Publisher :
Frontiers Media S.A., 2024.

Abstract

Rhamnolipids (RLs) are highly valuable molecules in the cosmetic, pharmaceutic, and agricultural sectors with outstanding biosurfactant properties. In agriculture, due to their potential to artificially stimulate the natural immune system of crops (also known as elicitation), they could represent a critical substitute to conventional pesticides. However, their current synthesis methods are complex and not aligned with green chemistry principles, posing a challenge for their industrial applications. In addition, their bioproduction is cumbersome with reproducibility issues and expensive downstream processing. This work offers a more straightforward and green access to RLs, crucial to decipher their mechanisms of action and design novel potent and eco-friendly elicitors. To achieve this, we propose an efficient seven-step synthetic pathway toward (R)-3-hydroxyfatty acid chains present in RLs, starting from cellulose-derived levoglucosenone, with Michael addition, Baeyer–Villiger oxidation, Bernet–Vasella reaction, and cross-metathesis homologation as key steps. This method allowed the production of (R)-3-hydroxyfatty acid chains and derivatives with an overall yield ranging from 24% to 36%.

Details

Language :
English
ISSN :
22962646
Volume :
12
Database :
Directory of Open Access Journals
Journal :
Frontiers in Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.31250632b3b44f6982b2626881ed808
Document Type :
article
Full Text :
https://doi.org/10.3389/fchem.2024.1362878