Abstract
FA selectivity of a Celite-immobilized potato lipid acyl hydrolase (LAH) in esterification reactions with long-chain FA, including stearic acid (18∶0), oleic acid (18∶1), linoleic acid (18∶2), α-linolenic acid (18∶3), EPA (20∶5), and DHA (22∶6), and alcohol co-substrates (n-propanol, isopropanol, 1,3-propanediol, and glycerol) was studied in isooctane. Immobilized LAH was selective for FA of greater degrees of unsaturation (18∶3>18∶2>18∶1>18∶0) for all alcohol acceptors evaluated. Selectivity of LAH toward unsaturated C18 FA increased with an increase in water activity (a w ) from 0.19 to 0.90 for n-propanol, isopropanol, and 1,3-propanediol as alcohol co-substrates. In contrast, with glycerol as the alcohol cosubstrate, selectivity of LAH toward these unsaturated C18 FA increased with a decrease in a w from 0.90 to 0.19. In addition, immobilized LAH strongly discriminated against EPA and DHA for both 1,3-propanediol and glycerol as alcohol co-substrates.
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References
Villeneuve, P., and T.A. Foglia, Lipase Selectivities: Potential Application in Lipid Bioconversions, INFORM 8:640–665 (1997).
Mukherjee, K.D., I. Kiewitt, and M.J. Hills, Substrate Specificities of Lipases in View of Kinetic Resolution of Unsaturated Fatty Acids, Appl. Microbiol. Biotechnol. 40:489–493 (1993).
Jachmanián, I., E. Schulte, and K.D. Mukherjee, Substrate Selectivity in Esterification of Less Common Fatty Acids Catalysed by Lipases from Different Sources, Appl. Microbiol. Biotechnol. 44:563–567 (1996).
Mukherjee, K.D., Plant Lipases and Their Application in Lipid Biotransformations, Prog. Lipid Res. 33:165–174 (1994).
Racusen, D., and M. Foote, A Major Soluble Glycoprotein of Potato Tubers, J. Food Biochem. 4:43–52 (1980).
Galliard, T., The Enzymic Deacylation of Phospholipids and Galactolipids in Plants: Purification and Properties of a Lipolytic Acyl-Hydrolase from Potato Tubers, Biochem. J. 12::379–390 (1971).
Galliard, T., Enzymic Deacylation of Lipids in Plants. The Effects of Free Fatty Acids on the Hydrolysis of Phospholipids by the Lipolytic Acyl Hydrolase of Potato Tubers, Eur. J. Biochem. 21:90–98 (1971).
Dennis, S., and T. Galliard, Wax Ester Formation Catalysed by Isoenzymes of Lipolytic Acyl Hydrolase, Phytochemistry 13:2469–2473 (1974).
Macrae, A.R., J.E. Visicchio, and A. Lanot, Application of Potato Lipid Acyl Hydrolase for the Synthesis of Monoacylglycerols, J. Am. Oil Chem. Soc. 75:1489–1494 (1988).
Pinsirodom, P., and K.L. Parkin, Fatty Acid and Product Selectivities of Potato Tuber Lipid Acyl Hydrolase in Esterification Reactions with Glycerol in Organic Media, 76:1119–1125 (1999).
Pinsirodom, P., and K.L. Parkin, Selectivity of Celite-Immobilized Patatin (lipid acyl hydrolase) from Potato (Solanum tuberosum L.) Tubers in Esterification Reactions as Influenced by Water Activity and Glycerol Analogues as Alcohol Acceptors, J. Agric. Food Chem. 48:155–160 (2000).
Andrews, D.L., B. Beames, M.D. Summers, and W.D. Park, Characterization of the Lipid Acyl Hydrolase Activity of the Major Potato (Solanum tuberosum) Tuber Protein, Patatin, by Cloning and Abundant Expression in a Baculovirus Vector, Biochem. J. 252:199–206 (1988).
Anderson, C., P. Pinsirodom, and K.L. Parkin, Hydrolytic Selectivity of Patatin (lipid acyl hydrolase) from Potato (Solanum tuberosum L.) Tubers Toward Various Lipids, J. Food Biochem. 26:63–74 (2002).
Galliard, T., The Enzymatic Breakdown of Lipids in Potato Tuber by Phospholipid-annd Galactolipid-Acyl Hydrolase Activities and by Lipoxygenase, Phytochemistry 9:1725–1734 (1970).
Willis, W.M., R.W. Lencki, and A.G. Marangoni, Lipid Modification Strategies in the Production of Nutrionanally Functional Fats and Oils, Crit. Rev. Food Sci. Nutr. 38:639–674 (1998).
Medina, A.R., A.G. Giménez, F.G. Camacho, and J.A.S. Pérez, Concentration and Purification of Stearidonic, Eicosapentaenoic, and Docosahexaenoic Acids from Cod Liver Oil and Marine Microalga Isochrysis galbana, J. Am. Oil Chem. Soc. 72:575–583 (1995).
Lepage, G., and C.C. Roy, Improved Recovery of Fatty Acid Through Direct Transesterification Without Prior Extraction or Purification, J. Lipid Res. 25:1391–1396 (1994).
Castillo, E., V. Dossat, A. Marty, J.S. Condoret, and D. Combes, The Role of Silica Gel in Lipase-Catalyzed Esterification Reactions of High-Polar Substrates, J. Am. Oil Chem. Soc. 74:77–85 (1977).
Rangheard, M.-S., G. Langrand, C. Triantaphylides, and J. Baratti, Multi-competitive Enzymatic Reactions in Organic Media: A Simple Test for the Determination of Lipase Fatty Acid Specificity, Biochim. Biophys. Acta 913:20–28 (1989).
Halling, P.J., Salt Hydrates for Water Activity Control with Biocatalysis in Organic Media, Biotechnol. Tech. 6:271–276 (1992).
van Heerden, E., and D. Litthauer, The Comparative Discriminating Abilities of Lipases in Different Media and Their Application in Fatty Acid Enrichment, Biocatal. Biotrans. 16:461–474 (1999).
Selmi, B., E. Gontier, F. Ergan, and D. Thomas, Effect of Fatty Acid Chain Length and Unsaturation Number on Triglyceride Synthesis Catalyzed by Immobilized Lipase in Solvent-Free Medium, Enzyme Microb. Technol. 23:182–186 (1998).
Pleiss, J., M. Fischer, and R.D. Schmid, Anatomy of Lipase Binding Sites: The Scissile Fatty Acid Binding Site, Chem. Phys. Lipids 93:67–80 (1998).
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Pinsirodom, P., Parkin, K.L. Selectivity of potato tuber lipid acyl hydrolase toward long-chain unsaturated FA in esterification reactions with glycerol analogs in organic media. J Amer Oil Chem Soc 80, 335–340 (2003). https://doi.org/10.1007/s11746-003-0699-8
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DOI: https://doi.org/10.1007/s11746-003-0699-8