Advertisement

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

Chapter
  • 403 Downloads
Part of the SpringerBriefs in Molecular Science book series (BRIEFSMOLECULAR)

Abstract

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.

Keywords

Glycerolysis Esterification Hydrolysis Interesterification Chemo-enzymatic Multistep synthesis 

References

  1. 1.
    Tonetto G, Ferreira ML (2010) Two-step synthesis of structured lipids of general structure MLM using enzymatic or combined enzymatic and chemical reactions. In: Hughes Victor C (ed) Sunflowers: cultivation, nutrition, and biodiesel uses. ISBN: 978-1-61761-543-6Google Scholar
  2. 2.
    Dan-Jinh Hu, Chen JM, Xia YM (2013) A comparative study on production of middle chain diacylglycerol through enzymatic esterification and glycerolysis. J Ind Eng Chem 19:1457–1463Google Scholar
  3. 3.
    Al Zuhair S, Taher H (eds) (2016) Supercritical fluids technology in lipase catalyzed processes. CRC, Taylor & Francis, USAGoogle Scholar
  4. 4.
    Wang W, Li T, Ning Z, Yang YWB, Yang X (2011) Production of extremely pure diacylglycerol from soybean oil by lipase-catalyzed glycerolysis. EMT 49:192–196Google Scholar
  5. 5.
    Liu N, Wang Y, Zhao QZ, Cui C, Fu M, Zhao MN (2012) Immobilisation of lecitase® ultra for production of diacylglycerols by glycerolysis of soybean oil. Food Chem 134:301–307CrossRefGoogle Scholar
  6. 6.
    von der Haar D, Stäbler A, Wichmann R, Schweiggert-Weisz U (2015) Enzyme-assisted process for DG synthesis in edible oils. Food Chem 176:263–270CrossRefGoogle Scholar
  7. 7.
    Zhong N, Gui Z, Xu L, Huan J, Kun H, Gao Y, Zhang X, Su J, Li B (2013) Solvent-free enzymatic synthesis of 1,3-diacylglycerols by direct esterification of glycerol with saturated fatty acids. Lipids Health Dis 12(65):7Google Scholar
  8. 8.
    Vázquez L, González N, Reglero G, Torres C (2016) Solvent-free lipase catalyzed síntesis of diacylglycerols as low-calorie food ingredient. Front Bioeng Biotechnol 4:6. doi: 10.3389/fbioe.2016.00006 CrossRefGoogle Scholar
  9. 9.
    Zeng CX, Qi SJ, Xin RP, Yang B, Wan YH (2015) Enzymatic selective synthesis of 1,3-DG based on deep eutectic solvent acting as substrate and solvent. Bioprocess Biosyst Eng 38:2053–2061CrossRefGoogle Scholar
  10. 10.
    Singh AK, Mukhopadhyay M (2012) Olive oil glycerolysis with the immobilized lipase Candida antarctica in a solvent-free system. Grasas Aceites 63(2):202–208CrossRefGoogle Scholar
  11. 11.
    Valério A, Fiametti KG, Rovani S, Franceschi E, Corazza ML, Treichel H et al (2009) Enzymatic production of mono- and diglycerides in compressed n-butane and AOT surfactant. J Supercrit Fluids 49:216–220CrossRefGoogle Scholar
  12. 12.
    Rendón X, López-Munguía A, Castillo E (2001) Solvent engineering applied to lipase-catalyzed glycerolysis of triolein. JAOCS 78(10):1061–1066Google Scholar
  13. 13.
    Wang W, Li T, Ning Z, Bo W, Yang Y, Yang X (2011) Production of extremely pure diacylglycerol from soybean oil by lipase-catalyzed glycerolysis. Enzym Microb Technol 49:192–196CrossRefGoogle Scholar
  14. 14.
    Voll F, Krüger RL, de Castilhos F, Cardozo Filho L, Cabral V, Ninow J, Corazza Marcos L (2011) Kinetic modeling of lipase-catalyzed glycerolysis of olive oil. Biochem Eng J 56:107–115CrossRefGoogle Scholar
  15. 15.
    Guo Z, Kahveci D, Ozcelik B, Xu X (2009) Improving enzymatic production of diglycerides by engineering binary ionic liquid medium system. New Biotechnol 26(1/2):37–44CrossRefGoogle Scholar
  16. 16.
    Calero J, Verdugo C, Luna D, Sancho ED, Luna C, Posadillo A, Bautista FM, Romero AA (2014) Selective ethanolysis of sunflower oil with Lipozyme RM IM, an immobilized Rhizomucor miehei lipase, to obtain a biodiesel-like biofuel, which avoids glycerol production through the monoglyceride formation. New Biotechnol 31(6):596–602CrossRefGoogle Scholar
  17. 17.
    Awadallak JA, Voll F, Ribas MC, da Silva C, Filho LC, da Silva EA (2013) Enzymatic catalyzed palm oil hydrolysis under ultrasound irradiation: diacylglycerol synthesis. Ultrason Sonochem 20:1002–1007CrossRefGoogle Scholar
  18. 18.
    Song Z, Liu Y, Jin Q, Li L, Wang X, Huang J, Liu R (2012) Lipase-catalyzed preparation of diacylglycerol-enriched oil from high-acid rice bran oil in solvent-free system. Appl Biochem Biotechnol 168:364–374CrossRefGoogle Scholar
  19. 19.
    Smith KW (2015) Specialty oils and fats in food and nutrition properties, processing and applications Woodhead publishing series in food science, technology and nutrition 8—structured triacylglycerols: properties and processing for use in food. pp 207–218Google Scholar
  20. 20.
    Kim BH, Akoh CC (2015) JFS special issue: 75 years of advancing food science, and preparing for the next 75 recent research trends on the enzymatic synthesis of structured lipids. J Food Sci 80(8):C1713–C1724CrossRefGoogle Scholar
  21. 21.
    Mohamed IO (2014) Enzymatic synthesis of cocoa butter equivalent from olive oil and palmitic-stearic fatty acid mixture. Appl Biochem Biotechnol 175(2):757–769CrossRefGoogle Scholar
  22. 22.
    Rezanka T, Lukavský J, Nedbalová L, Sigler K (2014) Production of structured triacylglycerols from microalgae. Phytochemistry 104:95–104CrossRefGoogle Scholar
  23. 23.
    Wei W, Feng Y, Zhang X, Cao X, Feng F (2015) Synthesis of structured lipid 1,3-dioleoyl-2-palmitoylglycerol in both solvent and solvent-free system. LWT-Food Sci Technol 60:1187–1194CrossRefGoogle Scholar
  24. 24.
    Liu S, Dong X, Wei F, Wang X, Lv X, Zhong J, Wua L, Quek S, Chen H (2015) Ultrasonic pretreatment in lipase-catalyzed synthesis of structured lipids with high 1,3-dioleoyl-2-palmitoylglycerol content. Ultrason Sonochem 23:100–108CrossRefGoogle Scholar
  25. 25.
    Wanga Y, Xia L, Xu X, Xie L, Duan Z (2012) Lipase-catalyzed acidolysis of canola oil with caprylic acid to produce medium-, long- and medium-chain-type structured lipids. Food Bioprod Process 90:707–712CrossRefGoogle Scholar
  26. 26.
    Camacho Paez B, Robles Medina A, Camacho Rubio F, Esteban Cerdá L, Molina Grima E (2003) Kinetics of lipase-catalysed interesterification of triolein and caprylic acid to produce structured lipids. J Chem Technol Biotechnol 78:461–470CrossRefGoogle Scholar
  27. 27.
    Camacho Paeza B, Robles Medina A, Camacho Rubio F, Gonzalez Moreno P, Molina Grima E (2002) Production of structured triglycerides rich in n-3 polyunsaturated fatty acids by the acidolysis of cod liver oil and caprylic acid in a packed-bed reactor: equilibrium and kinetics. Chem Eng Sci 57:1237–1249CrossRefGoogle Scholar
  28. 28.
    Sánchez D, Tonetto G, Ferreira ML (2014) Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in a organic solvent system. J Mol Catal B 100:7–18CrossRefGoogle Scholar
  29. 29.
    Moreno-Pérez S, Luna P, Señorans FJ, Guisán JM, Fernandez-Lorente G (2015) Enzymatic synthesis of triacylglycerols of docosahexaenoic acid: trans esterification of its ethyl esters with glycerol. Food Chem 187:559–565CrossRefGoogle Scholar
  30. 30.
    Moghaddama MG, Yekke Ghasemi Z, Khajeha M, Rakhshanipoura M, Yasin Y (2014) Application of response surface methodology in enzymatic synthesis: a review. Russ J Bioorganic Chem 40(3):252–262CrossRefGoogle Scholar
  31. 31.
    Karabulut I, Durmaz G, Hayaloglu AA (2009) Fatty acid selectivity of lipases during acidolysis reaction between oleic acid and monoacid triacylglycerols. J Agric Food Chem 57(21):10466–10470CrossRefGoogle Scholar
  32. 32.
    Muñío M d M, Robles A, Esteban L, González PA, Molina E (2009) Synthesis of structured lipids by two enzymatic steps: ethanolysis of fish oils and esterification of 2-monoacylglycerols. Process Biochem 44(7):723–730CrossRefGoogle Scholar
  33. 33.
    Gunstone F (ed) (2006) Modifying lipids for use in food. CRC, Boca RatonGoogle Scholar
  34. 34.
    Panesar PS, Marwaha SM, Chopra HK (eds) (2010) Enzymes in food processing fundamentals and potential applications. International Publishing, New DelhiGoogle Scholar
  35. 35.
    Tang W, Wang X, Huang J, Jin Q, Wang X (2015) A novel method for the synthesis of symmetrical triacylglycerols by enzymatic transesterification. Bioresour Technol 196:559–565CrossRefGoogle Scholar
  36. 36.
    Chaurasia SP, Bhandari K, Sharma A, Dalai AK (2016) A review on lipase catalysed synthesis of DHA rich glyceride from fish oils. IJRSI III(IA):9–20Google Scholar
  37. 37.
    Busch S, Horlacher P, Both S, Westfechtel A, Green US (2011) Synthesis routes toward triglycerides of conjugated linoleic acid. Eur J Lipid Sci Technol 113:92–99CrossRefGoogle Scholar
  38. 38.
    Hong SI, Kim Y, Yoon SW, Kim CSY (2012) Synthesis of CLA-enriched TAG by Candida antarctica lipase under vacuum. Eur J Lipid Sci Technol 114(9):1044–1051CrossRefGoogle Scholar
  39. 39.
    Wang X, Zou W, Sun X, Zhang Y, Wei L, Jin Q, Wang X (2015) Chemoenzymatic synthesis of 1,3-dioleoyl-2-palmitoylglycerol. Biotechnol Lett 37:691–696CrossRefGoogle Scholar
  40. 40.
    Halldorsson A, Magnusson CD, Haraldsson GG (2003) Chemoenzymatic synthesis of structured triacylglycerols by highly regioselective acylation. Tetrahedron 59:9101–9109CrossRefGoogle Scholar
  41. 41.
    Magnusson CD, Haraldsson GG (2010) Chemoenzymatic synthesis of symmetrically structured triacylglycerols possessing short-chain fatty acids. Tetrahedron 66:2728–2731CrossRefGoogle Scholar
  42. 42.
    Gudmundsdottir AV, Hansen KA, Magnusson CD, Haraldsson GG (2015) Synthesis of reversed structured triacylglycerols possessing EPA and DHA at their terminal positions. Tetrahedron 71:8544–8550CrossRefGoogle Scholar
  43. 43.
    Usai EM, Gualdi E, Solinas V, Battistel E (2010) Simultaneous enzymatic synthesis of FAME and triacetyl glycerol from triglycerides and methyl acetate. Bioresour Technol 101(20):7745–7750CrossRefGoogle Scholar
  44. 44.
    Akoh C, Sellapan S, Fomuso L, Yankah V (2002) Enzymatic synthesis of structured lipids. In: Kuo TM, Garner HW (eds) Lipid biotechnology. Marcel Dekker, New York, p 433Google Scholar
  45. 45.
    Shimada Y, Nagao T, Watanabe Y (2006) Application of multistep reactions with lipases to the oil and fat industry. In: Shaidi F (ed) Nutraceutical and Specialty lipids and their coproducts. Taylor and Francis, Boca RatonGoogle Scholar
  46. 46.
    Karabulul I, Durmaz G, Hayaloglu AA (2009) Fatty acid selectivity of lipases during Acidolysis reaction bewteen triolein and saturated fatty acids varying from caproic to behenic acids. J Agric Food Chem 57(16):7584–7590CrossRefGoogle Scholar
  47. 47.
    Akil E, Barea B, Finotelli P, Lecomte J, Torres AG, Villeneuve P (2016) Accesing regio and typo selectivity of Yarrowia lipolytica lipase in its free form and immobilized onto magnetic nanoparticles. Biochem Eng J 109:101–111CrossRefGoogle Scholar
  48. 48.
    Meng X, Xu G, Zhou QL, Wu JP, Yang LR (2014) Highly efficient solvent-free synthesis of 1,3-diacylglycerols by lipase immobilised on nano-sized magnetite particles. Food Chem 143:319–324CrossRefGoogle Scholar
  49. 49.
    Gupta S, Bhattacharya A, Murthy CN (2013) Tune to immobilize lipases on polymer membranes: techniques, factors and prospects. Biocatal Agric Biotechnol 2(3):171–190Google Scholar
  50. 50.
    Ríos GM, Belleville MP, Paolucci D (2012) Enzymatic membrane reactors in applications of membrane separations technology: recent advances, chapter 24. In: Mohanty K, Purkait M (eds) Membrane technologies and applications. CRC, Boca Raton, p 445Google Scholar
  51. 51.
    Hwang ET, Gu MB (2013) Enzyme stabilization by nano/microsized hybrid materials (review). Eng Life Sci 13(1):49–61CrossRefGoogle Scholar
  52. 52.
    Rodrigues RC, Fernández-Lafuente R (2010) Lipase from Rhizomucor miehei as a biocatalyst in fats and oils modification (Review). J Mol Catal B 66(1–2):15–32CrossRefGoogle Scholar
  53. 53.
    Fernandez-Lafuente R (2010) Lipase from thermomyces lanuginosus: uses and prospects as an industrial biocatalyst. J Mol Catal B 62(3–4):197–212CrossRefGoogle Scholar
  54. 54.
    Narancic T, Davis R, Nikodinovic-Runic J, O' Connor KE (2015) Recent developments in biocatalysis beyond the laboratory (review). Biotechnol Lett 37(5):943–954CrossRefGoogle Scholar

Copyright information

© The Author(s) 2017

Authors and Affiliations

  1. 1.PLAPIQUI-UNS-CONICETBuenos AiresArgentina

Personalised recommendations