본문 바로가기
KERD
논문KCI 등재

모노글리세리드와 카프릴산으로부터 고정화 리파제를 사용한 디글리세리드 생산

Synthesis of Diglyceride Containing Caprylic acid by Immobilized Lipase Catalyzed Esterification of Monoglyceride in a Solvent Free System

2

조회

0

다운로드

0

인용

0

참고문헌

키워드

주제분류생물학

초록

For the production of diglyceride (DG) containing medium chain fatty acid, which could be utilized as a substrate to structured lipid production, monoglyceride (MG) and caprylic acid were reacted in the presence of lipase. The reaction system was well mixed homogeneously without using any organic solvent. Among the lipases investigated, Lipozyme RM IM and Novozym 435 were selected on the basis of equilibrium DG yields from the medium chain fatty acid and MG. And reaction conditions such as addition of molecular sieve, water content of immobilized lipase, reaction temperature, and mole ratio of MG/caprylic acid are optimized to increase DG production by using Lipozyme RM IM. DG content of reaction mixture showed 8% increase by adding molecular sieve to reaction mixture. Removal of water from the immobilized lipase could affect seriously equilibrium content of DG. More than 2.8%(w/w) removal of water from the support could make 44% of DG. Optimum temperature was found to 60℃. Temperature shift from 60oC to 25℃ resulted in increase of free fatty acid (FFA) content. The equilibrium DG yield was not seriously affected by on MG/caprylic acid molar ratio. However, at the stoichiometric ratio of 1:1 the highest DG yield was obtained. Increasing MG/caprylic acid ratio from 0.3 to 1.8 decreased FFA content from 34% to 13%, while MG content increased from 27% to 50%.

Abstract

For the production of diglyceride (DG) containing medium chain fatty acid, which could be utilized as a substrate to structured lipid production, monoglyceride (MG) and caprylic acid were reacted in the presence of lipase. The reaction system was well mixed homogeneously without using any organic solvent. Among the lipases investigated, Lipozyme RM IM and Novozym 435 were selected on the basis of equilibrium DG yields from the medium chain fatty acid and MG. And reaction conditions such as addition of molecular sieve, water content of immobilized lipase, reaction temperature, and mole ratio of MG/caprylic acid are optimized to increase DG production by using Lipozyme RM IM. DG content of reaction mixture showed 8% increase by adding molecular sieve to reaction mixture. Removal of water from the immobilized lipase could affect seriously equilibrium content of DG. More than 2.8%(w/w) removal of water from the support could make 44% of DG. Optimum temperature was found to 60℃. Temperature shift from 60oC to 25℃ resulted in increase of free fatty acid (FFA) content. The equilibrium DG yield was not seriously affected by on MG/caprylic acid molar ratio. However, at the stoichiometric ratio of 1:1 the highest DG yield was obtained. Increasing MG/caprylic acid ratio from 0.3 to 1.8 decreased FFA content from 34% to 13%, while MG content increased from 27% to 50%.

참고문헌 (27)

  1. Anna, M. F, "Preparatioin of diglycerides by lipase-catalyzed alcoholysis of triglycerides", Enzyme Microb. Technol., 20, pp.198~206 (1997)
  2. Akoh, C. C, "Structured lipids. in: Food Lipids: Chemistry, Nutrition and Biotechnology", pp.877~908 (1998), Marcer Dekker, Inc
  3. Bradley, B. G, "Structured lipids: evidence evolving for widespread use. in: Structural Modified Food Fats: Synthesis, Biochemistry and Use" (1998), AOCS press
  4. Christensen, M. S, "Intestinal absorption and lymphatic transport of eicospentaenoic (EPA), Docosahexenoic (DHA), and Decanoic acids: dependence on intramolecular triacylglycerol structure", Am. J. Clin. Nutr., 61, pp.56~61 (1995)
  5. Farzaneh, S, "A New approach to the stereospecific synthesis of phospholipid the use of L-glyceric acid for the preparation of diacylglycerol", J. Org. Chem, 64, pp.7727~7737 (1999)
  6. Fomuso, L. B, "Structured lipids: lipase-catalyzed interesterification of tricaproin and trilinolein", J. Am. Oil Chem. Soc, 75, pp.405~410 (1998)
  7. Gunstone, F. D, "Movements towards tailor-made fats", Prog. Lipid Res, 37, pp.225~305 (1998)
  8. Haraldsson, G. G, "The Chemistry of the Functhonal Groups, Supplement B2: The Chemistry of Acid Derivatives. in: The Application Of Lipases in Organic Synthesis", pp.1395~1473 (1992), Biotech
  9. Haraldsson, G. G, "Chemoenzymatic synthesis of structured triacylglycerols containing eicosapentaenoic and docosahexaenoic acids", J. Am. Oil Chem. Soc, 77, pp.1157~1165 (2000)
  10. Husmann, B. F, "aspects of n-3 fatty acids", INFORM, 8, pp.428~447 (1997)
  11. Jennings, B, "Enzymatic modification of triacylglycerols of high eicosapentaenoic and docosahexaenoic acids content to produce structured lipids", J. Am. Oil Chem. Soc, 76, pp.1133~1137 (1999)
  12. Jose, A, "Rapid enzymatic production of acylglycerols from conjugated linoleic acid and glycerol in a solvent-free system", Biotechnol. Lett, 20, pp.617~621 (1998)
  13. Jose, A, "Continuous enzymatic exterification of glycerol with (poly)unsaturated fatty acids in a packed-bed reactor", Biotechnol. Bioeng, 68, pp.563~570 (1998)
  14. Jumpsen, J, "Brain development: Relationship to dietary lipid and lipid metabolism", pp.199~ (1995), AOCS Press
  15. Kang, S. T, "Effect of temperature on diacylglycerol production by enzymatic solid-phase glycerolysis of hydrogenated beet tallow", K. J. Food Sci. Tech., 26, pp.567~572 (1994)
  16. Kwon, S. J, "Production and in situ separation of mono- or diacylglycerol catalyzed by lipases in n-hexane", Enzyme Microb. Technol., 17, pp.700~704 (1995)
  17. Lee, K. T, "Immobilized lipase-catalyzed production of structured lipids with eicosapentaenoic acid at specific positions", J. Am. Oil Chem. Soc., 73, pp.611~615 (1998)
  18. Matthias, B., "Enzymatic esterification of glycerol l. lipase-catalyzed synthesis of regioisomerically pure 1,3-sn-diacylglycerols", J. Am. Oil Chem. Soc, 69, pp.955~960 (1992)
  19. McNeill, G. P, "Further improvements in the yield of monoglycerides during enzymatic glycerolysis of fats and oils", J. Am. Oil Chem. Soc, 68, pp.6~10 (1991)
  20. Mert, S, "A rapid method for enzymatic synthesis and purification of the structured triacylglycerol, 1,3-dilauroyl-2-oleoyl-glycerol", J. Am. Oil Chem. Soc, 76, pp.927~931 (1999)
  21. Nettleton, J. A, "Omega-3-fatty acids and health", pp.359~362 (1995), Chapman and Hall
  22. Rosu, R, "Enzymatic synthesis of symmetrical 1,3-diacylglycerols by direct esterification of glycerol in solvent-free system", J. Am. Oil Chem. Soc, 76, pp.839~843 (1999)
  23. Schmid, U, "Optimization of the reaction conditions in the lipase-catalyzed synthesis of structured triglycerides", J. Am. Oil Chem. Soc., 75, pp.1527~1531 (1998)
  24. Shimada, Y, "Production of structured lipid containing docosahexaenoic and caprylic acids using immobilized rhizopus delemar lipase", J. Ferment. Bioeng, 81, pp.299~303 (1996)
  25. Subramani, S, "Synthesis of structured lipids by transesterification of trilinolein catalyzed by lipozyme IM60", J. Agric. Food Chem., 49, pp.2071~2076 (2001)
  26. Yang, T. H, "Enzymatic synthesis of low-calorie structured lipids in a solvent-free system", J. Am. Oil Chem. Soc, 78, pp.291~296 (1999)
  27. Yamane, T, "High-yield diacylglycerol formation by solid-phase enzymatic glycerolysis of hydrogenated beef tallow", J. Am. Oil Chem. Soc, 71, pp.339~342 (1994)

관련 논문AI추천

대두유에서 글리세롤리시스 반응을 이용한 디글리세리드의 효소적 생산강성태, 권기석, 김강성, 박경준, 안은경한국미생물·생명공학회 · 한국미생물·생명공학회지2004 · 제32권 제1호회분식 반응기를 이용한 Glyceryl Monooleate와 Conjugated Linoleic Acid로부터 효소적 반응을 통한 디글리세롤 유지의 합성이기택, 전미선한국식품저장유통학회 · Food Science and Preservation2009 · 제16권 제2호Effect of microwave irradiation on lipase-catalyzed reactions in ionic liquids구윤모, 김영민, 안광민, 하성호한국분석과학회 · 분석과학2017 · 제30권 제3호Synthesis of Short-Chain Alkyl Butyrate through Esterification Reaction Using Immobilized Rhodococcus Cutinase and Analysis of Substrate Specificity through Molecular Docking김형권, 원석재, Yim Joung Han한국미생물·생명공학회 · Journal of Microbiology and Biotechnology2023 · 제33권 제2호실리카 코팅된 자성 나노입자로의 효소 고정화에 사용된 작용기가 리파아제의 활성과 안정성에 미치는 영향김문일, 김영민, 윤국로, 이승호, 이혜린, 최재영, 하성호, 홍상은한국분석과학회 · 분석과학2016 · 제29권 제3호Synthesis of Isoamyl Fatty Acid Ester, a Flavor Compound, by Immobilized Rhodococcus Cutinase김형권, Jeon Ye Won, Kim Yeong A, Lee Ka Yeong, Song Ha Min한국미생물·생명공학회 · Journal of Microbiology and Biotechnology2024 · 제34권 제6호

이 간행물의 다른 논문 (17건)