Submitted to: Biotechnology Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: June 6, 2003
Publication Date: August 20, 2003
Citation: NUNEZ, A., FOGLIA, T.A., ASHBY, R.D. ENZYMATIC SYNTHESIS OF A GALACTOPYRANOSE SOPHOROLIPID FATTY ACID-ESTER. BIOTECHNOLOGY LETTERS. v. 25. p. 1291-1297. Interpretive Summary: Fat and vegetable oil production in the United States far exceeds domestic consumption and their disposition by exportation is limited by strong competition with foreign markets. Accordingly, new uses for domestic fats and oils need to be developed. Biotechnology is an environmentally friendly approach that can increase the usage of these commodities by transforming them to higher value-added products with industrial potential. In our laboratory, a yeast, when grown on fat or oil substrates, produces a biodegradable sugar-lipid compound with surfactant type properties, but this natural product has limited solubility in water, a critical factor for its industrial use. In this work, the sugar-lipid complex was transformed using an enzymatic natural approach to add an additional sugar molecule to the structure. The resulting novel product has improved water solubility that expands its potential applications in the area of biodegradable detergents or agrochemicals.
Technical Abstract: A C18:1 sophorolipid lactone produced by the yeast Candida bombicola was deacetylated and ring opened with sodium methoxide to the methyl ester form. After re-acetylation with vinyl acetate using an immobilized lipase, the methyl ester was transesterified with 1,2-3,4-di-O-isopropylidene-D-galactopyranose in tetrahydrofuran using the same lipase catalyst. The sophorolipid derivative sugar-ester was hydrolyzed to give a galactopyranose sophorolipid ester as the final product