Optimisation of n-octyl oleate enzymatic synthesis over Rhizomucor miehei lipase

Bioprocess and Biosystems Engineering

Volumn 29, Issue 2, 2006, Pages 119-127

  Laudani, Chiara Giulia ^a,b   Habulin, Maja ^a   Primožič, Mateja ^a   Knez, Željko ^a   Della Porta, Giovanna ^b   Reverchon, Ernesto ^b  

^a UNIVERSITY OF MARIBOR   (Slovenia)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

Biocatalysis; Immobilised lipase; Kinetics; n Octyl oleate; Optimisation

Indexed keywords

CARBON DIOXIDE; CATALYST ACTIVITY; DRUG PRODUCTS PLANTS; ESTERIFICATION; OPTIMIZATION; ORGANIC COMPOUNDS; REACTION KINETICS; SUBSTRATES; SYNTHESIS (CHEMICAL);

BIOCATALYSIS; IMMOBILISED LIPASE; N-OCTYL OLEATE; RHIZOMUCOR MIEHEI LIPASE;

ENZYME KINETICS;

ALKYL GROUP; CARBON DIOXIDE; FATTY ACID; FATTY ACID ESTER; HEXANE; LUBRICATING AGENT; OCTANE; OCTANOL; OCTYL OLEATE; OLEIC ACID; ORGANIC COMPOUND; SOLVENT; SUPERCRITICAL CARBON DIOXIDE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BIOCATALYST; COMPARATIVE STUDY; CONCENTRATION (PARAMETERS); COSMETIC INDUSTRY; DRUG INDUSTRY; ENZYME MECHANISM; ENZYME SYNTHESIS; ESTERIFICATION; KINETICS; NONHUMAN; PARAMETER; PRIORITY JOURNAL; PROCESS MONITORING; PROCESS OPTIMIZATION; RHIZOMUCOR; RHIZOMUCOR MIEHEI; SCREENING; STIRRED REACTOR; TEMPERATURE; WATER CONTENT;

1-OCTANOL; ESTERIFICATION; FUNGAL PROTEINS; LIPASE; OLEIC ACIDS; RHIZOMUCOR;

RHIZOMUCOR MIEHEI;

EID: 33745726131     PISSN: 16157591     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00449-006-0061-4     Document Type: Article

References (41)

1. Wong CH, Whitesides GM (1994) Enzyme in synthetic organic chemistry. Tetrahedron organic chemistry series. Pergamon, Oxford
2. Shaw JF, Wang DL, Wang YJ (1991) Lipase-catalyzed ethanolysis and isopropanolysis of triglycerides with long chain fatty acid. Enzyme Microb Technol 13:544-546
3. Langrand G, Triantaphylides C, Baratti J (1988) Lipase catalyzed formation flavour esters. Biotechnol Lett 10:549-554
4. Garcia T, Martinez M, Aracil J (1993) Enzymatic synthesis of an analogue of jojoba oil: optimization by statistical analysis. Enzyme Microb Technol 15:607-611
5. Habulin M, Krmelj V, Knez Ž (1996) Synthesis of oleic acid esters catalyzed by immobilized lipase. J Agric Food Chem 44:338-342
6. Yahya ARM, Anderson WA, Moo-Young M (1998) Ester synthesis in lipase-catalyzed reactions. Enzyme Microb Technol 23:438-450
7. Gandhi NN, Patil NS, Sawant SB, Joshi JB, Wangikar PP, Mukesh D (2000) Lipase catalyzed esterification. Catal Rev 42:439-480
8. Cho SW, Rhee JS (1993) Immobilization of lipase for effective interesterification of fats and oils in organic solvent. Biotechnol Bioeng 41:204-210
9. Ergan F, Trani M, Andre G (1990) Production of glycerides from glycerol and fatty acid by immobilized lipases in non-aqueous media. Biotechnol Bioeng 35:195-200
10. Habulin M, Knez Ž (1993) Influence of reaction parameters on synthesis of n-butyl oleoate by immobilized Mucor-miehei lipase. Fat Sci Technol 95:249-252
11. Bloomer S, Adlercreutz P, Mattiason B (1992) Facile synthesis of fatty acid esters in high yields. Enzyme Microb Technol 14:546-552
12. Chulalaksananukul W, Condoret JS, Combes D (1992) Kinetics of geranyl acetate synthesis by lipase-catalysed transesterification in n-hexane. Enzyme Microb Technol 14:293-298
13. Knez Ž, Habulin M, Završnik D, Lavrič B (1990) Synthesis of oleic esters with immobilized lipase. Fat Sci Technol 92:169-172
14. Habulin M, Knez Ž (1991) High-pressure enzymatic hydrolysis of oil. J Memb Sci 61:315-324
15. Rocha JMS, Gil MH, Garcia FAP (1999) Optimisation of the enzymatic synthesis of n-octyl oleate with immobilised lipase in the absence of solvents. J Chem Technol Biotechnol 74:607-612
16. Rocha JMS, Gil MH, Garcia FAP (1994) Synthesis of n-octyl oleate with lipase from Mucor miehei immobilized onto polyethylene based graft copolymers. Biocatalysis 9:157-167
17. Yong YP, Al-Duri B (1996) Kinetic studies on immobilised lipase esterification of oleic acid and octanol. J Chem Technol Biotechnol 65:239-248
18. Knez Ž, Habulin M, Primožič M (2005) Enzymatic reactions in dense gases. Biochem Eng J 27:120-126
19. Jarzebski A, Malinowski JJ (1995) Potentials and prospects for application of supercritical fluid technology in bioprocessing. Proc Biochem 30:343-352
20. Leitgeb M, Knez Ž (1990) The influence of water on the synthesis of n-Butyl oleate by immobilized Mucor miehei Lipase. J Am Oil Chem Soc 67:775-778
21. Yadav GD, Lathi PS (2004) Synthesis of citronellol laurate in organic media catalyzed by immobilized lipases: kinetic studies. J Mol Cat B-Enz 27:113-119
22. Gandhi NN, Sawant SB, Joshi JB (1995) Studies on the lipozyme-catalyzed synthesis of butyl laurate. Biotechnol Bioeng 46:1-12
23. Knez Ž, Rizner V, Habulin M, Bauman D (1995) Enzymatic synthesis of oleyl oleate in dense fluids. J Am Oil Chem Soc 72:1345-1349
24. Bailey JE, Ollis DF (1986) The kinetics of enzyme catalysed reactions. In: Biochemical engineering fundamentals. McGraw-Hill, New York, 2nd (edn), Chapter3, pp 132-137
25. Yadav GD, Devi KM (2004) Kinetics of hydrolysis of tetrahydrofurfuryl butyrate in a three phase system containing immobilized lipase from Candida Antarctica. Bioch Eng J 17:57-63
26. Knez Ž, Habulin M (2002) Compressed gases as alternative enzymatic-reaction solvents: a short review. J Supercritic Fluids 23:29-42
27. Triantafyllou AO, Wehtje E, Adlercreutz P, Mattiasson B (1995) Effects of sorbitol addition on the action of free and immobilized hydrolytic enzymes in organic media. Biotechnol Bioeng 45:406-414
28. Basheer S, Mogi K, Nakajima M (1995) Surfactant-modified lipase for the catalysis of the interesterification of triglycerides and fatty acids. Biotechnol Bioeng 45:187-195
29. Winkler FK, Gubernator K (1994) In: Woolley P, Petersen SB (eds) Lipases: their structure, biochemistry and application. Cambridge University Press, Cambridge, pp 139-157
30. Zaks A, Klibanov AM (1988) Enzymatic catalysis in nonaqueous solvents. J Biol Chem 263:3194-3201
31. Carta G, Gainer JL, Benton AH (1991) Enzymatic synthesis of esters using an immobilized lipase. Biotechnol Bioeng 37:1004-1009
32. 2. Biotechnol Bioeng 39:273-280
33. Marty A, Combes D, Condoret JS (1994) Continuous reaction-separation process for enzymatic esterification in supercritical carbon dioxide. Biotechnol Bioeng 43:497-504
34. Valivety RH, Halling PJ, Peilow AD, Macrae AR (1992) Lipases from different sources vary widely in dependence of catalytic activity on water activity. Biochimica et Biophysica Acta (BBA)- Prot Struct Mol Enzymol 1122:143-146
35. Goddard R, Bosley J, Al-Duri B (2000) Esterification of oleic acid and ethanol in plug flow (packed bed) reactor under supercritical conditions: Investigation of kinetics. J Supercritic Fluids 18:121-130
36. Ramamurthi S, McCurdy AR (1994) Lipase-catalyzed esterification of oleic acid and methanol in hexane - a kinetic study. J Am Oil Chem Soc 71:927-930
37. Cleland W (1983) Substrate inhibition. In: Colowick SP, Kaplan NO (eds) Contemporary enzyme kinetics and mechanism. Academic Press, Orlando, pp 253-265
38. Chulalaksananukul W, Condoret JS, Delorme P, Willemot RM (1990) Kinetic study of esterification by immobilized lipase in n-hexane. FEBS Lett 276:181-184
39. Martinelle M, Hult K (1995) Kinetics of acyl transfer reactions in organic media catalysed by Candida antarctica lipase B. Biochimica et Biophysica Acta (BBA)- Prot Struct Mol Enzymol 1251:191-197
40. Cornish-Bowden A (1995) Introduction to enzyme kinetics. In: Fundamentals of enzyme kinetics, chapter 2. Portland Press, London, pp 30-37
41. Srivastava S, Madras G, Modak J (2003) Esterification of myristic acid in supercritical carbon dioxide. J Supercritic Fluids 27:55-64