Abstract
Modified Candida rugosa and Pseudomonas cepacia lipase (CRL and PCL) were co-lyophilized with two pairs of synthetic diastereoisomeric amphiphiles, d- and l-2-(2,3,4,5,6-pentahydroxy-hexanoylamino)-propyl]-carbamoyl-propionylamino)-pentanedioic acid didodecyl ester (d- and l-BIG2C12CA); d- and l-2-(2,3,4,5,6-pentahydroxy-hexanoylamino)-pentanedioic acid didodecyl ester (d- and l-2C12GE). Enzyme activities of the modified lipase in the transesterification in organic solvent were evaluated. Both pairs of the diastereoisomeric amphiphiles showed enhanced enzyme activity in the transacetylation between racemic sulcatol and isopropenyl acetate in diisopropyl ether, catalyzed by the PCL-co-lyophilizate, by 19–48 fold when compared to the native lipase lyophilized from buffer alone independent of the stereochemistry of the amphiphiles, while in the case of the CRL-co-lyophilizate only the l-BIG2C12CA showed enhanced enzyme activity in the transbutyrylation between racemic solketal and vinyl butyrate in cyclohexane as high as 68–78 fold.
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References
Adlercreutz P (1996) Modes of using enzymes in organic media. In: Koskinen AMP, Klibanov AM, eds. Enzymatic Reactions in Organic Media. Glasgow: Blackie Academic & Professional, pp. 9–42.
Brockerhoff H, Jensen RG (1974) IV. Lipases. In: Brockerhoff H, Jensen RG, eds. Hydrolytic Enzymes. New York: Academic Press, pp. 152–155.
Fukunaga K, Mine Y, Samejima K, Yoshimoto M, Nakao K, Sugimura Y (2002) Enhancement of Candida rugosa lipase activity in non-aqueous media by co-lyophilization with amphiphiles from aqueous solution. Biotechnol. Lett. 24: 1157–1160.
Klibanov AM (1996) Prospects and challenges of biocatalysis in organic media. In: Koskinen AMP, Klibanov AM, eds. Enzymatic Reactions in Organic Media. Glasgow: Blackie Academic & Professional, pp. 308–310.
Longhi S, Fusetti F, Grandori R, Lotti M, Vanoni M, Alberghina L (1992) Cloning and nucleotide sequences of two lipase genes from Candida cylindracea. Biochim. Biophys. Acta 1131: 227–232.
Mine Y, Fukunaga K, Yoshimoto M, Nakao K, Sugimura Y (2001) Modification of lipases with poly(ethylene glycol) and poly(oxyethylene) detergents and their catalytic activities in organic solvents. J. Biosci. Bioeng. 92: 539–543.
Mingarro I, Abad C, Braco L (1995) Interfacial activation-based molecular bioimprinting of lipolytic enzymes. Proc. Natl. Acad. Sci. USA 92: 3308–3312.
Mingarro I, González-Navarro H, Braco L (1996) Trapping of different lipase conformers in water-restricted environments. Biochemistry 35: 9935–9945.
Okahata Y, Fujimoto Y, Ijiro K (1995) A lipid-coated lipase as an enentioselective ester synthesis catalyst in homogeneous organic solvents. J. Org. Chem. 60: 2244–2250.
Pencreac'h G, Baratti JC (1996) Hydrolysis of p-nitrophenyl palmitate in n-heptane by the Pseudomonas cepacia lipase: a simple test for the determination of lipase activity in organic media. Enzyme Microb. Technol. 18: 417–422.
Sarda L, Desnelle P (1958) Action de la lipase pancreatique sur les esters en emulsion. Biochim. Biophys. Acta 30: 513–521.
Sugimura Y, Fukunaga K, Matsuno T, Nakao K, Goto M, Nakashio F (2000) A study on the surface hydrophobicity of lipases Biochem. Eng. J. 5: 227–232.
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Mine, Y., Fukunaga, K., Yoshimoto, M. et al. Stereochemistry of a diastereoisomeric amphiphile and the species of the lipase influence enzyme activity in the transesterification catalyzed by a lipase-co-lyophilizate with the amphiphile in organic media. Biotechnology Letters 25, 1863–1867 (2003). https://doi.org/10.1023/A:1026241914262
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DOI: https://doi.org/10.1023/A:1026241914262