Submitted to: Book Chapter
Publication Type: Book / Chapter
Publication Acceptance Date: 4/15/2005
Publication Date: 6/15/2005
Citation: Hou, C.T. 2005. Value-added industrial products through biocatalysis: production of novel fatty acids. In: Hou, C.T., editor, Handbook of Industrial Biocatalysis, New York, NY: Taylor & Francis/CRC, Inc. p. 1-25.
Technical Abstract: The United States produces more than 18 billion pounds of soybean oil (SBO) annually with a yearly carryover of more than 300 million pounds. How to utilize this surplus oil effectively becomes a large economic issue in the agricultural community. SBO are a relatively cheap raw material at 22 to 25 cents per pound and are an attractive candidate for bioindustries. The content of unsaturated fatty acids for SBO are oleic acid 22% and linoleic acids 55%. SBO and its components fatty acids can be converted to value-added products such as oxygenated fatty acids through bioprocesses. Alpha-, betta- and omega-hydroxy fatty acids, as well as dicarboxylic acids have been produced by bioprocesses. In this chapter, we described the production of novel oxygenated fatty acid products by microbial biotransformation. Unsaturated fatty acids such as oleic, linoleic and/or linolenic acids are converted by microbial enzymes to monohydroxy and/or monoketo fatty acids. A microbial isolate, Pseudomonas aeruginosa PR3, converted oleic acid to a new product, 7,10-dihydroxy-8(E)-octadecinoic acid (DOD) through an intermediate, 10-hydroxy-8(E)-octadecinoic acid. DOD has anti-microbial activity. DOD might be used as raw material for synthesis of industrial products such as rigid polyurethane foams. Strain PR3 also converted ricinoleic acid to 7,10,12-trihydroxy-8(E)-octadecinoic acid, which possesses anti-plant pathogenic fungal activity. Another microorganism, Clavibacter sp. ALA2, converted linoleic acid to many novel products such as: 12,13,17-trihydroxy-9(Z)-octadecinoic acid , 12,13,16-trihydroxy-9(Z)-octadecinoic acid, two tetrahydrofuranyl fatty acids (THFAs), 12-hydroxy-13,16-epoxy-9(Z)- octadecenoic acid and 7,12-dihydroxy-13,16-epoxy-9(Z)-octadecenoic acid; and two diepoxy bicyclic fatty acids, 12,17;13,17-diepoxy-9(Z)-octadecenoic acid (DEOA) and 12,17;13,17-diepoxy-7-hydroxy-9(Z)-octadecenoic acid (hDEOA). Strain ALA2 also converts other n-3 and n-6 polyunsaturated fatty acids such as alpha- and gamma-linolenic acid, EPA, DHA, and arachidonic acid to many novel trihydroxy-, epoxy-, and tetrahydrofuranyl-fatty acids products. Tetrahydrofuranyl compounds are known to have anticancer activity. The diepoxy bicyclic fatty acids are completely new chemical entities. With many functionality groups on the molecules, their application in biomedical as well as specialty chemical industries is expected.