The catalytic activity of lipases toward hydroxy fatty acids—A review
- 1 May 1996
- journal article
- review article
- Published by Wiley in Journal of Oil & Fat Industries
- Vol. 73 (5) , 543-549
- https://doi.org/10.1007/bf02518105
Abstract
Hydroxy fatty acids, derived from several natural and synthetic sources, have many applications. Lipases have been employed to catalyze reactions involving hydroxy acids to narrowly shape the product distribution via their regio‐ and stereoselectivities. This manuscript reviews the action of lipase on hydroxy acids and their derivatives. The formation of estolides or lactones by lipase‐catalyzed reactions depends strongly on the position of the hydroxyl moiety on the hydroxy acyl group and slightly on the hydroxy acid chainlength and concentration.Pseudomonas sp. and porcine pancreatic lipases are the most useful for catalyzing formation of optically pure lactones, while lipases lacking positional selectivity catalyzed estolide formation best. The product distribution of lipase‐catalyzed esterification between hydroxy‐ and nonhydroxy‐acyl groups is strongly dependent on the lipase type. Lipase‐catalyzed reactions between hydroxy acids and alcohols yield hydroxy esters, not estolides, as the major product.Keywords
This publication has 55 references indexed in Scilit:
- Macrocyclic lactone synthesis by lipases in water-in-oil microemulsionsBiochimica et Biophysica Acta (BBA) - Lipids and Lipid Metabolism, 1995
- Lipase‐catalyzed Kinetic Resolution of 3‐Hydroxy Esters: Optimization, Batch, and Continuous ReactionsaAnnals of the New York Academy of Sciences, 1995
- Enzyme-catalysed condensation polymerization of 11-hydroxyundecanoic acid with lipase from Candida cylindraceaPolymer, 1994
- Synthesis of Uncommon Wax Esters with Immobilized LipasesAnnals of the New York Academy of Sciences, 1992
- Enzymatic monoacylation of trihydroxy compoundsBiotechnology Letters, 1992
- A remarkable short synthesis of optically active mevinic acid analogs by biocatalytic lactonization of syn-3,5-dihydroxy estersThe Journal of Organic Chemistry, 1991
- Simple synthesis of (R)-5-hexadecanolide.Agricultural and Biological Chemistry, 1990
- Preparation of enantiomerically enriched compounds by using enzymes. Part VIII. Lipase-catalyzed kinetic resolution of 2-hydroxyhexadecanoic acid and its esters.Agricultural and Biological Chemistry, 1990
- Enzymatic preparation of ethyl (S)-3-hydroxybutanoate with a high enantiomeric excess.Agricultural and Biological Chemistry, 1989
- Polymerization of 10-hydroxydecanoic acid in benzene with polyethylene glycol-modified lipaseBiotechnology Letters, 1985