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This brief presents the state of the art on enzymatic synthesis of structured triglycerides and diglycerides, focusing on glycerol as the substrate and covering interesterification of vegetable oils in one and two steps. It critically reviews the available literature on enzymatic and chemo-enzymatic synthesis of di- and triglycerides in one or more steps. The effects of the structure, length and unsaturation of the fatty acids are carefully considered, as well as the inhibitory potential of highly unsaturated complex fatty acid structures.

The brief also addresses acyl migration and the use of adsorbents, taking into account the most recent literature and presenting the problem in an industrial context. It discusses experimental and analytical problems concerning, e.g. the lab scale and the scaling up to bench and pilot plants. Several examples are presented, and their successes and failures are assessed. Biocatalysts based on lipases are analyzed with regard to problems of immobilization, stability on storage time and activity after multiple uses. The need for specific Sn-2 lipases is presented and strategies for optimizing Sn-2 esterification are discussed. Lastly, practical aspects are examined, e.g. lipase “leaching” with loss of activity, taking into account the latest findings on continuous and batch reactor configurations and presenting the advantages and disadvantages of each.



Chapter 1. What Is The Importance of Structured Triglycerides and Diglycerides?

This chapter reviews several important aspects of structured triglycerides (STs) and diglycerides (SDs), with the most updated literature on the topic. STs and SDs are synthesized to achieve some specific metabolic effects or to enhance physical–chemical properties of fats and oils. They comprise cocoa butter equivalents, human milk fat substitutes, low-calorie fats and oils, health-beneficial fatty acid-rich fats/oils, or diglyceride oil, and margarines or other plastic fats. A review of the metabolic fate of triglycerides and the health and nutritional properties of structured tri and diglycerides is presented.Structured triglycerides can be synthesized by diverse routes, depending on the sort of triglycerides and the nature of the substrate. Several approaches to the productions of STs and SDs are described briefly including chemical and enzymatic interesterification (involving acidolysis and glycerolysis), hydrolysis and esterification.In addition, the consumer market for structured di- and triglycerides is revised.

María Luján Ferreira, Gabriela Marta Tonetto

Chapter 2. Literature Review: What Has Been Explored About Enzymatic Synthesis of ST and SD?

This chapter focuses on the enzymatic synthesis of triglycerides and diglycerides in one or more steps. It also discusses the attempts to introduce chemical steps to reduce relative costs. The main costs in practical, industrial environments are the solvent and the enzymes. The reactions are studied in either solvent or solvent-free media, especially in the last 5 years.The main substrates are glycerol and vegetable oils. There is a trend in using biomass or waste from other industries instead of edible oils, especially due to the impact of using high-value nutritional oils as a source. In this sense, the best option seems to be the use of glycerol, a low-cost source of acyl groups and a low-cost source of lipase, and to avoid solvents. However, with the goal of a high conversion of glycerol to the required structured di- and triglycerides, this is not an easy task. Problems like lipase inhibition by glycerol or acyl compounds, the required immobilization of the enzyme, the needed reuse of the immobilized lipase and an adequate level of mixing to achieve the required reaction media are being increasingly studied. Strategies to improve reuse, enzymatic activity in reuse and stability in storage are being more and more explored.The review is thought to cover mainly the last 5–10 years with the most important advances in context, especially in the field of immobilized enzyme applications and other post-immobilization treatments.

María Luján Ferreira, Gabriela Marta Tonetto

Chapter 3. What Problems Arise When Enzymatic Synthesis of Structured Di- and Triglycerides Is Performed?

This chapter describes the batch and continuous reactors used in structured diglyceride and triglyceride (ST) synthesis, and analyzes and discusses the several problems found in the literature and in the practical settings for the production of STs, especially when scaling to industry is considered. The problems of adsorbent use, the reaction media composition, the relative adsorption of substrates and products, the secondary contamination due to protein leaching in some immobilized systems, the perturbations introduced by the adsorbents, the main problems of enzyme inhibition or inactivation due to glycerol/fatty acids and several others are discussed in this chapter.

María Luján Ferreira, Gabriela Marta Tonetto

Chapter 4. Potential Solutions to Drawbacks What Can Be Done About the Drawbacks in ST and SD Enzymatic Synthesis?

This chapter evaluates the potential solutions to the several drawbacks reported in the literature and known by the authors due to their research activity related to laboratory testing of lipases in ST and SD synthesis. These solutions are analyzed in terms of their advantages and disadvantages and with the economical aspects properly considered.Nowadays ,the issue of trans fatty acids is very important. These fatty acids are generated during hydrogenation by isomerization and industry is required to explore different processes other than hydrogenation of fats. Interesterification as an alternative to hydrogenation is suitable for health-concerned customers, and random or chemical interesterification is the most used process. It is less complicated and expensive and is easier than enzymatic interesterification.ST and SD synthesis has been prepared using chemical interesterification. However, the potential solution to the high cost involved in enzymatic reactions could be addressed if non-expensive local new enzymes are obtained (using recombination or exploring new sources of lipases such as local plants). In addition, the use of cheaper substrates and other reaction routes would add a potential improvement in cost (such as glycerol). The innovation of the use of multiphasic reactors could add an important solution to the need for the reuse of immobilization.

María Luján Ferreira, Gabriela Marta Tonetto

Chapter 5. Industrial Perspectives Which Have to Be Taken into Account to Scale from the Laboratory to Industry?

This chapter considers the industrial perspectives available on the topic from the point of view of the authors in terms of the feasibility of a stronger interaction between industry and academia in order to focus the research on the solution of industrial problems.

María Luján Ferreira, Gabriela Marta Tonetto

Chapter 6. Examples of Successful Industrial Synthesis of Structured Diglycerides and Triglycerides

This chapter analyzes the success of some industrial applications of enzymes in the production of SD and ST, and the conditions of this achievement.

María Luján Ferreira, Gabriela Marta Tonetto

Chapter 7. Conclusions

The perspectives of lipases in the food industry related to glycerides were very promising 10 years ago. Today, the market is wide and demanding for high-quality, “healthy” food products. The progress of the research on the value of “healthy” foods with the new findings in the roles of ω3, ω6 and ω9 fatty acids in health and disease are fueling this interest. The importance of structured glycerides as sources of fatty acids is of paramount importance, the metabolism of them being more and more elucidated. Among them, diglycerides seem competitive compared to triglycerides as sources if the processing aspects are improved, especially when high-temperature deodorization should be avoided. The glycerides including polyunsaturated (PUFA) or monounsaturated (MUFA) could be important tools in weight control and hypertension if their benefits are confirmed, but how, when and with what other compounds (such as antioxidants) should be properly clarified. In this sense, even monoglycerides obtained through enzymatic processes could have interesting markets, but the main problem of the high cost of the enzyme is still present as it has always been. Beyond food applications, the field of biolubricants and long alcohol esters of fatty acids could have importance in the renewed interest in lipases at the industrial level in the future.

María Luján Ferreira, Gabriela Marta Tonetto


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