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United States Department of Agriculture

Agricultural Research Service

Title: Lipase-Catalyzed Production of Novel Hydroxylated Fatty Amides in Organic Solvent

Authors
item Levinson, William
item Kuo, Tsung Min
item Kurtzman, Cletus

Submitted to: Enzyme and Microbial Technology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: February 1, 2005
Publication Date: March 3, 2005
Citation: Levinson, W.E., Kuo, T., Kurtzman, C.P. 2005. Lipase-catalyzed production of novel hydroxylated fatty amides in organic solvent. Enzyme and Microbial Technology. 37:126-130.

Interpretive Summary: Surplus vegetable oils represent attractive renewable resources for the production of useful chemicals. We are investigating microbial conversion of vegetable oils and their component fatty acids for producing value-added products. Previously, we developed the scale-up bioprocesses for producing novel multi-hydroxyl fatty acids possessing surface-active property and antifungal activity. In this study, we further investigated the reaction parameters for directly adding ammonia to the reactive terminus of the fatty acids by use of enzymes to form new compounds called fatty amides with enhanced ability to undergo chemical reactions. The results led to the enzymatic production of a group of novel hydroxyl fatty amides. The impact of this study provides basic information and technology for scientists to develop bioprocesses for producing similar types of new compounds from low cost vegetable oils.

Technical Abstract: Pseudozyma (Candida) antarctica lipase B is known to catalyze the direct amidation of carboxylic acids with ammonia in organic solvents. We tested this system for production of primary fatty amides from hydroxy fatty acids including the naturally occurring monohydroxy fatty acids, ricinoleic acid (RA) and lesquerolic acid (LQA) and the novel multihydroxy fatty acids, 7,10-dihydroxy-8(E)-octadecenoic acid (DOD) and 7,10,12-trihydroxy-8(E)-octadecenoic acid (TOD). Reactions were performed at temperatures up to 55 deg C. Ricinoleic acid and lesquerolic acid were transformed at initial rates comparable to or better than that of oleic acid, a non-hydroxylated substrate. Transformation percentage at 7 days was better than 95% for all substrates except TOD (93.9%). At 55 deg C, most reactions approached completion within 1 day. The primary amides of LQA, DOD, and TOD are novel compounds having melting points of 73, 105, and 100 deg C, respectively.

Last Modified: 7/30/2014
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