Substrate selectivity of various lipases in the esterification of cis- and trans-9-octadecenoic acid

Applied Microbiology and Biotechnology

Volumn 51, Issue 4, 1999, Pages 480-485

  Borgdorf, R ^a   Warwel, S ^a  

^a Fed Ctr Cereal   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BUTANOL; CARICA PAPAYA EXTRACT; ELAIDIC ACID; HEXANE; OLEIC ACID; PANCREAS ENZYME; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; CATALYST; CHEMICAL BOND; CIS TRANS ISOMERISM; ENZYME IMMOBILIZATION; ENZYME SPECIFICITY; ESTERIFICATION; MUCOR; NONHUMAN; PSEUDOMONAS; REACTION TIME; SWINE;

BACTERIA; ESTERIFICATION; FUNGI; KINETICS; LIPASE; OLEIC ACID; PLANTS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

ANIMALIA; CANDIDA; CANDIDA ANTARCTICA; CANDIDA CYLINDRACEA; CARICA PAPAYA; MUCOR; PSEUDOMONAS; PSEUDOMONAS SP.; RHIZOMUCOR MIEHEI; SUIDAE; SUS SCROFA;

EID: 0032956666     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s002530051420     Document Type: Article

References (33)

1. Briand D, Dubreucq E, Grimaud J, Galzy P (1995) Substrate specificity of the lipase from Candida parapsilosis. Lipids 30: 747-754
2. Brockerhoff H (1970) Substrate specificity of pancreatic lipase: influence of the structure of fatty acids on the reactivity of esters. Biochim Biophys Acta 212: 92-101
3. Charton E, Macrae AR (1992) Substrate specificities of lipases A and B from Geotrichum candidum CMICC 335426. Biochim Biophys Acta 1123: 59-64
4. Charton E, Macrae AR (1993) Specificities of immobilized Geotrichum candidum CMICC 335426 lipases A and B in hydrolysis and ester synthesis reactions in organic solvents. Enzyme Microb Technol 15: 489-493
5. Deleuze H, Langrand G, Millet H, Baratti J, Buono G, Triantaphylides C (1987) Lipase-catalyzed reactions in organic media: competition and applications. Biochim Biophys Acta 911: 117-120
6. Hassanien FR, Mukherjee KD (1986) Isolation of lipase from germinating oilseeds for biotechnological processes. J Am Oil Chem Soc 63: 893-897
7. Heimermann WH, Holman RT, Gordon DT, Kowalyshyn DE, Jensen RG (1973) Effect of double bond position in octadecenoates upon hydrolysis by pancreatic lipase. Lipids 8: 45-47
8. Hills MJ, Kiewitt I, Mukherjee KD (1990) Lipase from Brassica napus L. discriminates against cis-4 and cis-6 unsaturated fatty acids and secondary and tertiary alcohols. Biochim Biophys Acta 1042: 237-240
9. Holmquist M (1998) Insights into the molecular basis for fatty acyl specificities of lipases from Geotrichum candidum and Candida rugosa. Chem Phys Lipids 93: 57-65
10. Jachmanián I, Mukherjee KD (1996) Esterification and interesterification reactions catalyzed by acetone powder from germinating rapeseed. J Am Oil Chem Soc 73: 1527-1532
11. Jachmanín I, Schulte E, Mukherjee KD (1996) Substrate selectivity in esterification of less common fatty acids catalysed by lipases from different sources. Appl Microbiol Biotechnol 44: 563-567
12. Jensen RG (1974) Characteristics of the lipase from the mold, Geotrichum candidum: a review. Lipids 9: 149-157
13. Jensen RG, Sampugna J, Pereira RL (1964) Pancreatic lipase. Lipolysis of synthetic triglycerides containing a trans fatty acid. Biochim Biophys Acta 84: 481-483
14. Jensen RG, Sampugna J, Quinn JG, Carpenter DL, Marks TA, Alford JA (1965) Specificity of a lipase from Geotrichum candidum for cis-octadecenoic acid. J Am Oil Chem Soc 42: 1029-1032
15. Jensen RG, Gordon DT, Heimermann WH, Holman RT (1972) Specificity of Geotrichum candidum lipase with respect to double bond position in triglycerides containing cis-octadecenoic acids. Lipids 7: 738-741
16. Kazlauskas RJ, Bornscheuer UT (1998) Biotransformations with lipases. In: Rehm HJ, Reed G (eds) Biotechnology, vol 8a, 2nd edn. VCH, Weinheim, pp 37-191
17. Kleimann R, Earle FR, Tallent WH, Wolff IA (1970) Retarded hydrolysis by pancreatic lipase of seed oils with trans-3 unsaturation. Lipids 5: 513-518
18. Labuschagne RB, van Tonder A, Litthauer D (1997) Flavobacterium odoratum lipase: isolation and characterization. Enzyme Microb Technol 21: 52-58
19. Lands WEM (1979) Selective recognition of geometric and positional isomers of fatty acids in vitro and in vivo. In: Emken EA, Dutton HJ (eds) Geometrical and positional fatty acid isomers. The American Oil Chemists' Society, Champaign, Ill., pp 181-212
20. Mozaffar Z, Weete JD (1993) Purification and properties of an extracellular lipase from Pythium ultimum. Lipids 28: 377-382
21. Mukherjee KD (1990) Lipase-catalyzed reactions for modification of fats and other lipids. Biocatalysis 3: 277-293
22. Mukherjee KD, Kiewitt I (1996a) Enrichment of very-long-chain mono-unsaturated fatty acids by lipase-catalysed hydrolysis and transesterification. Appl Microbiol Biotechnol 44: 557-562
23. Mukherjee KD, Kiewitt I (1996b) Specificity of Carica papaya latex as biocatalyst in the esterification of fatty acids with 1-butanol. J Agric Food Chem 44: 1948-1952
24. Mukherjee KD, Kiewitt I, Hills MJ (1993) Substrate specificities of lipases in view of kinetic resolution of unsaturated fatty acids. Appl Microbiol Biotechnol 40: 489-493
25. Pedersen S, Hølmer G (1995) Studies of the fatty acid specificity of the lipases from Rhizomucor miehei toward 20:1n-9, 20:5n-3, 22:1n-9 and 22:6n-3. J Am Oil Chem Soc 72: 239-243
26. Piazza GJ, Bilyk A, Brower DP, Haas MJ (1992) The positional and fatty acid selectivity of oat seed lipase in aqueous emulsions. J Am Oil Chem Soc 69: 978-981
27. Pleiss J, Fischer M, Schmid RD (1998) Anatomy of lipase binding sites: the scissile fatty acid binding site. Chem Phys Lipids 93: 67-80
28. Rangheard M-S, Langrand G, Triantaphylides C, Baratti J (1989) Multi-competitive enzymatic reactions in organic media: a simple test for the determination of lipase fatty acid specificity. Biochim Biophys Acta 1004: 20-28
29. Röbbelen G (1984) Biogenese und Verfügbarkeit pflanzlicher Fettrohstoffe. Fette Seifen Anstrichmittel 86: 373-379
30. Schmid RD, Verger R (1998) Lipases: interfacial enzymes with attractive applications. Angew Chem Int Ed Engl 37: 1608-1633
31. Sidebottom CM, Charton E, Dunn PPJ, Mycock G, Davies C, Sutton JL, Macrae AR, Slabas AR (1991) Geotrichum candidum produces several lipases with markedly different substrate selectivities. Eur J Biochem 202: 485-491
32. Sonnet PE, Foglia TA, Feairheller SH (1993a) Fatty acid selectivity of lipases: erucic acid from rapeseed oil. J Am Oil Chem Soc 70: 387-391
33. Sonnet PE, Foglia TA, Baillargeon MW (1993b) Fatty acid selectivity: the selectivity of lipases of Geotrichum candidum. J Am Oil Chem Soc 70: 1043-1045