Submitted to: Journal of Organic Chemistry
Publication Type: Peer reviewed journal
Publication Acceptance Date: 7/1/2002
Publication Date: 7/11/2003
Citation: SINGH, S.K., FELSE, P.A., GROSS, R.A., NUNEZ, A., FOGLIA, T.A. REGIOSELECTIVE ENZYME-CATALYZED SYNTHESIS OF SOPHOROLIPID ESTERS, AMIDES, AND MULTIFUNCTIONAL MONOMERS. JOURNAL OF ORGANIC CHEMISTRY. 2003. V. 68(14). p. 5466-5477. Interpretive Summary: The production of fats and oils in the United States far exceeds domestic consumption. Export previously has been relied upon for their disposition but currently there is strong competition with foreign oilseed production. Accordingly, new nonfood uses for domestic fats and oils need to be developed. Biotechnology is one approach that can increase the usage of these commodities by transforming them to value-added products with industrial potential. In this work yeast was grown on a fat or oil substrate to produce a biodegradable sugar-lipid molecule with surfactant type properties. The same sugar-lipid complex subsequently was transformed enzymatically into a series of sugar lipid nitrogen containing derivatives. To this end it was necessary to characterize the compounds prepared using sophisticated analytical techniques that were developed in this laboratory. These products have potential applications in the areas of polymers, detergents, and pharmaceuticals.
Technical Abstract: Enzyme-mediated synthetic routes were developed for the preparation of a new family of glycolipid derivatives. The ethyl ester of sophorolipid was subjected to Novozym 435 catalyzed amidation in dry THF with tyramine, phenethylamine, 4-fluorophenethylamine, 2-(p-tolyl)ethylamine, or 4- methoxyphenethylamine to generate corresponding secondary amides selectively. The amide formed between tyramine and the sophorolipid ethyl ester was subjected to Novozym 435 mediated acylation with vinyl methacrylate to form corresponding 6', 6'' diacyl derivatives regioselectively. The efficient formation of the same diacyl derivatives was also achieved in a one-pot reaction by enzyme-catalyzed amidation followed by acylation.