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United States Department of Agriculture

Agricultural Research Service

Research Project: BIOCATALYTIC FUNCTIONALIZATION OF PLANT LIPIDS
2008 Annual Report


1a.Objectives (from AD-416)
To demonstrate the technical feasibility of using isolated enzymes in nonaqueous media to functionally modify vegetable oils on a scale suitable for commercial deployment. Optimize a pilot-scale system for non-aqueous enzymatic transformation of soybean oil to high value products with novel functional groups and properties, such as feruloylated monoacyl- and diacylglycerides, for food and non-food applications. Create a flexible, durable and environmentally benign platform technology for the bioelectrocatalytic transformation of plant triglycerides and phospholipids to higher-value products.


1b.Approach (from AD-416)
Processes for producing modified plant lipids with novel and valuable functional properties are essential for developing new markets for commodity vegetable oils. Furthermore, these processes and products should have minimal adverse impact on the environment and pose no threat to plant operators and the surrounding community. It is the premise of this proposal that using isolated enzymes in selected nonaqueous media can meet these design goals. Two distinctly different approaches are considered. One approach, for enzymes not having complex cofactor requirements, employs soybean oil as a solvent as well as a reactant, while the other approach, for enzymes having more substantial structural and cofactor needs, places the enzyme in a highly structured environ and specifically tailored media. In the first approach, synthesis of a patented product is examined to optimize reaction variables for pre-commercial production. The second approach addresses several fundamental issues regarding ex vivo use of membrane-associated enzymes for the bioelectrocatalytic transformation of phospholipids and triglycerides. Taken together, new knowledge will be gained and useful processes will be developed that can deliver value-added vegetable oil derivatives for consumers and industry.


3.Progress Report
Processes for improved production of a new skincare product were developed at the National Center for Agricultural Utilization Research (Peoria, IL). This work was conducted with the Biotechnology Research and Development Consortium under a Cooperative Research and Development Agreement.

Conducted research to demonstrate the feasibility of using vegetable oils having one (of three) fatty acid groups removed as an improvement in the enzymatic reaction of ferulic acid with soybean oil in the production of skincare products. Conditions for optimally removing the single fatty acid and isolating the desired product were identified.

Work to further our understanding of foundational steps needed for developing an electrode system consisting of immobilized enzymes in liquid salts has led to the following results: .
1)work to evaluate how an altered electrode surface chemistry can affect surface-supported lipid thin films has shown that an equal mix of carboxyl and hydroxyl groups did not affect surface-supported lipid thin films, but a slight alteration of the lipid composition did – adding a “marginal” amount of negatively charged lipids caused rounded lipid thin films to flatten on the altered surface;.
2)work evaluating the role that lipid composition plays in the interaction between a liquid salt and a surface-supported lipid thin film has shown that the net charge and intrinsic bending properties of the lipid influenced the interaction;.
3)work evaluating the influence of liquid salts on the physical state of organized lipids has shown that liquid salts, added after lipids have formed an organized structure, can cause the lipids to gradually shift from a “liquid” to a “gel” state, and liquid salts added prior to lipids forming an organized structure can influence the overall organization of the lipids. This research addresses NP 306, Component 2.


4.Accomplishments
1. PRODUCTION OF DIACYLGLYCEROLS (DAG) BY ENZYMATIC ALCOHOLYSIS AND ISOLATION BY MOLECULAR DISTILLATION OR LIQUID CARBON DIOXIDE. DAG has been shown to be particularly useful in the preparation of new biobased products from vegetable oil. We replaced conventional processing steps, which employ harsh chemical treatments, with processes that rely on enzymes and benign extraction methods. These new processing procedures were shown to produce superior products. This offers a convenient method for companies to expedite development of lipid-based food, pharmaceutical and cosmetic ingredients. The research addresses NP 306,Component 2, Problem Areas 2a and 2c.

2. INDIVIDUAL COMPONENTS OF LIQUID SALTS AFFECT THIN FILMS DIFFERENTLY. Enzymes can be immobilized on a surface and put into a liquid salt to modify vegetable oils. Some enzymes in liquid salts may require a protective “layer” (called a membrane) to fully function. We determined that individual components of liquid salts can distinctly disrupt one type of protective layer. With this information, we will be able to better design a benign platform system that modifies vegetable oils for use in cosmetic ingredients. The research addresses NP 306, Component 2, Problem Areas 2a and 2c.

3. CATALYST ASSISTED PYROLOSIS OF RENEWABLE RESOURCES. There is an immediate need for alternative sources of fuels and chemical feed stocks. Pyrolysis of renewable resources such as vegetable oils, lignin and cellulose is one route to bio-based fuels and fine chemicals. Our research allowed for the rapid screening of catalysts and characterization of the pyrolytic products. From these efforts, proper catalyst choice will lead to greater product selectivity and reduced energy input for the pyrolytic conversion of biomass to bio-fuels and fine chemical feedstocks. The research addresses NP 306, Component 2, Problem Areas 2a and 2c.


5.Significant Activities that Support Special Target Populations
None.


6.Technology Transfer

Number of Active CRADAs1
Number of New Patent Applications Filed1
Number of Non-Peer Reviewed Presentations and Proceedings3

Review Publications
Laszlo, J.A., Compton, D.L., Vermillion, K. 2008. Acyl migration kinetics of vegetable oil 1,2-diacylglycerols. Journal of the American Oil Chemists' Society. 85(4):307-312.

Laszlo, J.A., Evans, K.O. 2007. Influence of self-assembled monolayer surface chemistry on Candida antarctica lipase B adsorption and specific activity. Journal of Molecular Catalysis B: Enzymatic. 48:84-89.

Evans, K.O. 2008. Supported phospholipid bilayer interaction with components found in typical room-temperature ionic liquids - a QCM-D and AFM study. International Journal of Molecular Sciences. 9:498-511.

Compton, D.L., Laszlo, J.A., Eller, F.J., Taylor, S.L. 2008. Purification of 1,2-diacylglycerols from vegetable oils: comparison of molecular distillation and liquid CO2 extraction. Industrial Crops and Products. 28(2):113-121.

Last Modified: 4/18/2014
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