Synthesis of a novel macrolactone by lipase-catalyzed intra-esterification of hydroxy-fatty acid in organic media.
The unsaturations and groups bound to the ring and to the lateral chain of lactones give a large diversity in this class of molecules. In this work we produced enzymatically a macrolactone in organic media. The substrate used was a hydroxy-fatty acid: (+)-coriolic acid and the enzymes tested were free or immobilized microbial lipases. The immobilized lipase from Candida antarctica seems to be the most adequate catalyst offering a high reaction yield. The intra-esterification was studied as a function of temperature and type of solvent. Higher yields were obtained when using diisopropyl-ether at 35 degrees C. This reaction, involving an alcohol group on an internal position on the carbon chain of the substrate hydroxy-acid, produces an original lactone: 13S-octadeca-(9Z,11E)-dienolide. The product was purified and characterized using (1)H nuclear magnetic resonance spectroscopy, mass spectrometry and infrared spectroscopy.
Gargouri
Mohamed
M
Biological Engineering Unit, National Institute of Applied Sciences and Technology (INSAT), BP 676, 1080 Tunis Cedex, Tunisia. mohamed.gargouri@insat.rnu.tu
Drouet
Philippe
P
Legoy
Marie-Dominique
MD
D000475:Alkenes; D001709:Biotechnology; D002175:Candida / Q000378:metabolism; D004800:Enzymes, Immobilized / Q000378:metabolism; D005231:Fatty Acids, Unsaturated / Q000737:chemistry; D066298:In Vitro Techniques; D007783:Lactones / Q000737:chemistry* / Q000378:metabolism*; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013055:Spectrophotometry, Infrared; D013379:Substrate Specificity; D013696:Temperature
C447921:13-octadeca-9,11-dienolide; D000475:Alkenes; D004800:Enzymes, Immobilized; D005231:Fatty Acids, Unsaturated; D007783:Lactones; C447920:coriolic acid; D008049:Lipase