Altering the substrate specificity of Candida rugosa LIP4 by engineering the substrate-binding sites

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 13, 2007, Pages 5103-5108

  Lee, Li Chiun ^a   Chen, Yu Ting ^b   Yen, Chih Chung ^c   Chiang, Teresa Ching Yn ^d   Tang, Shye Jye ^a   Lee, Guan Chiun ^e   Shaw, Jei Fu ^a,b,f  

^a NATIONAL TAIWAN OCEAN UNIVERSITY   (Taiwan)

^b NATIONAL CHUNG HSING UNIVERSITY   (Taiwan)

^c NATIONAL CHIAYI UNIVERSITY   (Taiwan)

^d UNIVERSITY OF WISCONSIN MADISON   (United States)

^e MING CHUAN UNIVERSITY   (Taiwan)

^f INSTITUTE OF PLANT AND MICROBIAL BIOLOGY   (Taiwan)

Author keywords

Candida rugosa; Lipase; Pichia pastoris; Saturation mutagenesis; Substrate specificity

Indexed keywords

FUNGAL PROTEIN; LIP4 PROTEIN, CANDIDA RUGOSA; RECOMBINANT PROTEIN; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; CANDIDA; CHEMISTRY; ENZYME SPECIFICITY; ENZYMOLOGY; GENETICS; METABOLISM; POINT MUTATION; SITE DIRECTED MUTAGENESIS;

BINDING SITES; CANDIDA; FUNGAL PROTEINS; LIPASE; MUTAGENESIS, SITE-DIRECTED; POINT MUTATION; RECOMBINANT PROTEINS; SUBSTRATE SPECIFICITY;

CANDIDA; CANDIDA CYLINDRACEA; CANDIDA RUGOSA; PICHIA PASTORIS;

EID: 34447309751     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0702949     Document Type: Article

References (40)

1. Dominguez de Maria, P.; Sanchez-Montero, J. M.; Sinisterra, J. V.; Alcantara, A. R. Understanding Candida rugosa lipases: an overview. Biotechnol. Adv. 2006, 24, 180-196.
2. Akoh, C. C.; Lee, G. C.; Shaw, J. F. Protein engineering and applications of Candida rugosa lipase isoforms. Lipids 2004, 39, 513-526.
3. Barton, M. J.; Hamman, J. P.; Fichter, K. C.; Calton, G. J. Enzymatic resolution of (R,S)-2-(4-hydroxyphenoxy) propionic acid. Enzyme Microb. Technol. 1990, 12, 577-583.
4. Chang, R. C.; Chou, S. J.; Shaw, J. F. Multiple forms and functions of Candida rugosa lipase. Biotechnol. Appl. Biochem. 1994, 19, 93-97.
5. Diczfalusy, M. A.; Hellman, U.; Alexson, S. E. Isolation of carboxylester lipase (CEL) isoenzymes from Candida rugosa and identification of the corresponding genes. Arch. Biochem. Biophys. 1997, 348, 1-8.
6. Hernaiz, M. J.; Sanchez Montero, J. M.; Sinisterra, J. V. New differences between isoenzymes A and B from Candida rugosa lipase. Biotechnol. Lett. 1997, 19, 303-306.
7. Lopez, C.; Guerra, N. P.; Rua, M. L. Purification and characterization of two isoforms from Candida rugosa lipase B. Biotechnol. Lett. 2000, 22, 1291-1294.
8. Longhi, S.; Fusetti, F.; Grandori, R.; Lotti, M.; Vanoni, M.; Alberghina, L. Cloning and nucleotide sequences of two lipase genes from Candida cylindracea. Biochim. Biophys. Acta 1992, 1131, 227-232.
9. Brocca, S.; Grandori, R.; Breviario, D.; Lotti, M. Localization of lipase genes on Candida rugosa chromosomes. Curr. Genet. 1995, 28, 454-457.
10. Lotti, M.; Grandori, R.; Fusetti, F.; Longhi, S.; Brocca, S.; Tramontano, A.; Alberghina, L. Cloning and analysis of Candida cylindracea lipase sequences. Gene 1993, 124, 45-55.
11. Lotti, M.; Tramontano, A.; Longhi, S.; Fusetti, F.; Brocca, S.; Pizzi, E.; Alberghina, L. Variability within the Candida rugosa lipases family. Protein Eng. 1994, 7, 531-535.
12. Xin, J. Y.; Xiao-Xue Hu, Y. X.; Cui, J. R.; Li, S. B.; Xia, C. G.; Zhu, L. M. Fine separation and characterization of Candida rugosa lipase isoenzymes. J. Basic Microbiol. 2002, 42, 355-363.
13. Hernaiz, M. J.; Rua, M.; Celda, B.; Medina, P.; Sinisterra, J. V.; Sanchez-Montero, J. M. Contribution to the study of the alteration of lipase activity of Candida rugosa by ions and buffers. Appl. Biochem. Biotechnol. 1994, 44, 213-229.
14. Lee, G. C.; Tang, S. J.; Sun, K. H.; Shaw, J. F. Analysis of the gene family encoding lipases in Candida rugosa by competitive reverse transcription-PCR. Appl. Environ. Microbiol. 1999, 65, 3888-3895.
15. de Maria, P. D.; Sanchez-Montero, J. M.; Alcantara, A. R.; Valero, F.; Sinisterra, J. V. Rational strategy for the production of new crude lipases from Candida rugosa. Biotechnol. Lett. 2005, 27, 499-503.
16. Chang, S. W.; Lee, G. C.; Shaw, J. F. Efficient production of active recombinant Candida rugosa LIP3 lipase in Pichia pastoris and biochemical characterization of the purified enzyme. J. Agric. Food Chem. 2006, 54, 5831-5838.
17. Chang, S. W.; Lee, G. C.; Shaw, J. F. Codon optimization of Candida rugosa lip1 gene for improving expression in Pichia pastoris and biochemical characterization of the purified recombinant LIP1 lipase. J. Agric. Food Chem. 2006, 54, 815-822.
18. Chang, S. W.; Shieh, C. J.; Lee, G. C.; Shaw, J. F. Multiple mutagenesis of the Candida rugosa LIP1 gene and optimum production of recombinant LIP1 expressed in Pichia pastoris. Appl. Microbiol. Biotechnol. 2005, 67, 215-224.
19. Lee, G. C.; Lee, L. C.; Sava, V.; Shaw, J. F. Multiple mutagenesis of non-universal serine codons of the Candida rugosa LIP2 gene and biochemical characterization of purified recombinant LIP2 lipase overexpressed in Pichia pastoris. Biochem. J. 2002, 366, 603-611.
20. Tang, S. J.; Shaw, J. F.; Sun, K. H.; Sun, G. H.; Chang, T. Y.; Lin, C. K.; Lo, Y. C.; Lee, G. C. Recombinant expression and characterization of the Candida rugosa lip4 lipase in Pichia pastoris: comparison of glycosylation, activity, and stability. Arch. Biochem. Biophys. 2001, 387, 93-98.
21. Tang, S. J.; Sun, K. H.; Sun, G. H.; Chang, T. Y.; Lee, G. C. Recombinant expression of the Candida rugosa lip4 lipase in Escherichia coli. Protein Expr. Purif. 2000, 20, 308-313.
22. Brocca, S.; Schmidt-Dannert, C.; Lotti, M.; Alberghina, L.; Schmid, R. D. Design, total synthesis, and functional overexpression of the Candida rugosa lip1 gene coding for a major industrial lipase. Protein Sci. 1998, 7, 1415-1422.
23. Ghosh, D.; Wawrzak, Z.; Pletnev, V. Z.; Li, N.; Kaiser, R.; Pangborn, W.; Jornvall, H.; Erman, M.; Duax, W. L. Structure of uncomplexed and linoleate-bound Candida cylindracea cholesterol esterase. Structure 1995, 3, 279-288.
24. Grochulski, P.; Li, Y.; Schrag, J. D.; Bouthillier, F.; Smith, P.; Harrison, D.; Rubin, B.; Cygler, M. Insights into interfacial activation from an open structure of Candida rugosa lipase. J. Biol. Chem. 1993, 268, 12843-12847.
25. Mancheno, J. M.; Pernas, M. A.; Martinez, M. J.; Ochoa, B.; Rua, M. L.; Hermoso, J. A. Structural insights into the lipase/ esterase behavior in the Candida rugosa lipases family: crystal structure of the lipase 2 isoenzyme at 1.97A resolution. J. Mol. Biol. 2003, 332, 1059-1069.
26. Pletnev, V.; Addlagatta, A.; Wawrzak, Z.; Duax, W. Three-dimensional structure of homodimeric cholesterol esterase-ligand complex at 1.4 Å resolution. Acta Crystallogr. D: Biol. Crystallogr. 2003, 59, 50-56.
27. Cygler, M.; Schrag, J. D. Structure and conformational flexibility of Candida rugosa lipase. Biochim. Biophys. Acta 1999, 1441, 205-214.
28. Johannes, T. W.; Zhao, H. Directed evolution of enzymes and biosynthetic pathways. Curr. Opin. Microbiol. 2006, 9, 261-267.
29. Reetz, M. T. Controlling the enantioselectivity of enzymes by directed evolution: practical and theoretical ramifications. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5716-5722.
30. Kretz, K. A.; Richardson, T. H.; Gray, K. A.; Robertson, D. E.; Tan, X.; Short, J. M. Gene site saturation mutagenesis: a comprehensive mutagenesis approach. Methods Enzymol. 2004, 388, 3-11.
31. Redondo, O.; Herrero, A.; Bello, J. F.; Roig, M. G.; Calvo, M. V.; Plou, F. J.; Burguillo, F. J. Comparative kinetic study of lipases A and B from Candida rugosa in the hydrolysis of lipid p-nitrophenyl esters in mixed micelles with Triton X-100. Biochim. Biophys. Acta 1995, 1243, 15-24.
32. Tiss, A.; Carriere, F.; Verger, R. Effects of gum arabic on lipase interfacial binding and activity. Anal. Biochem. 2001, 294, 36-43.
33. Cygler, M.; Grochulski, P.; Kazlauskas, R. J.; Schrag, J. D.; Bouthillier, F.; Rubin, B.; Serreqi, A. N.; Gupta, A. K. A structural basis for the chiral preferences of lipases. J. Am. Chem. Soc. 1994, 116, 3180-3186.
34. Manetti, F.; Mileto, D.; Corelli, F.; Sore, S.; Palocci, C.; Cernia, E.; D'Acquarica, I.; Lotti, M.; Alberghina, L.; Botta, M. Design and realization of a tailor-made enzyme to modify the molecular recognition of 2-arylpropionic esters by Candida rugosa lipase. Biochim. Biophys. Acta 2000, 1543, 146-158.
35. Schmitt, J.; Brocca, S.; Schmid, R. D.; Pleiss, J. Blocking the tunnel: engineering of Candida rugosa lipase mutants with short chain length specificity. Protein Eng. 2002, 15, 595-601.
36. DeSantis, G.; Wong, K.; Farwell, B.; Chatman, K.; Zhu, Z.; Tomlinson, G.; Huang, H.; Tan, X.; Bibbs, L.; Chen, P.; Kretz, K.; Burk, M. J. Creation of a productive, highly enantioselective nitrilase through gene site saturation mutagenesis (GSSM). J. Am. Chem. Soc. 2003, 125, 11476-11477.
37. Marcus, S. L.; Polakowski, R.; Seto, N. O.; Leinala, E.; Borisova, S.; Blancher, A.; Roubinet, F.; Evans, S. V.; Palcic, M. M. A single point mutation reverses the donor specificity of human blood group B-synthesizing galactosyltransferase. J. Biol. Chem. 2003, 278, 12403-12405.
38. Garrett, J. B.; Kretz, K. A.; O'Donoghue, E.; Kerovuo, J.; Kim, W.; Barton, N. R.; Hazlewood, G. P.; Short, J. M.; Robertson, D. E.; Gray, K. A. Enhancing the thermal tolerance and gastric performance of a microbial phytase for use as a phosphate-mobilizing monogastric-feed supplement. Appl. Environ. Microbiol. 2004, 70, 3041-3046.
39. Arezi, B.; Hansen, C. J.; Hogrefe, H. H. Efficient and high fidelity incorporation of dye-terminators by a novel archaeal DNA polymerase mutant. J. Mol. Biol. 2002, 322, 719-729.
40. Kazlauskas, R. Biological chemistry: enzymes in focus. Nature 2005, 436, 1096-1097.