Synthesis of a novel macrolactone by lipase-catalyzed intra-esterification of hydroxy-fatty acid in organic media.

Abstract:

: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.

journal_name

J Biotechnol

journal_title

Journal of biotechnology

authors

Gargouri M,Drouet P,Legoy MD

doi

10.1016/s0168-1656(01)00374-1

subject

Has Abstract

pub_date

2002-01-18 00:00:00

pages

259-66

issue

3

eissn

0168-1656

issn

1873-4863

pii

S0168165601003741

journal_volume

92

pub_type

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