Optimizing lipases and related enzymes for efficient application

Trends in Biotechnology

Volumn 20, Issue 10, 2002, Pages 433-437

  Bornscheuer, Uwe T ^a   Bessler, Cornelius ^a   Srinivas, Ramisetti ^b   Hari Krishna, Sajja ^a  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCATALYSTS; OPTIMIZATION;

REACTION MEDIUM;

ENZYMES;

ENZYME; ESTERASE; MICROBIAL ENZYME; PHOSPHOLIPASE; SOLVENT; TRIACYLGLYCEROL LIPASE;

ENZYME;

BIOCATALYST; DERIVATIZATION; DIRECTED MOLECULAR EVOLUTION; ENANTIOSELECTIVITY; ENZYME ACTIVATION; ENZYME ENGINEERING; ENZYME IMMOBILIZATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; ESTERIFICATION; GENE EXPRESSION; HYDROLYSIS; MOLECULAR BIOLOGY; NITRATION; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; SOLUBILIZATION;

BACTERIA; DATABASES, PROTEIN; DIRECTED MOLECULAR EVOLUTION; ENZYME STABILITY; ENZYMES, IMMOBILIZED; FUNGI; LIPASE; PROTEIN ENGINEERING; SPECIES SPECIFICITY;

EID: 0036773518     PISSN: 01677799     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0167-7799(02)02046-2     Document Type: Review

References (62)

1. Bornscheuer U.T., Kazlauskas R.J. Hydrolases in Organic Synthesis - Regio- and Stereoselective Biotransformations. 1999;Wiley-VCH.
2. Liese A., et al. Industrial Biotransformations. 2000;Wiley-VCH.
3. Balkenhohl F., et al. Optically active amines via lipase-catalyzed methoxyacetylation. J. Prakt. Chem. 339:1997;381-384.
4. Burton S.G., et al. The search for the ideal biocatalyst. Nat. Biotechnol. 20:2002;37-45.
5. Schmid R.D., Verger R. Lipases: Interfacial enzymes with attractive applications. Angew. Chem. Int. Ed. Engl. 37:1998;1608-1633.
6. Reetz M.T. Lipases as practical biocatalysts. Curr. Opin. Chem. Biol. 6:2002;145-150.
7. Drauz, K. and Waldmann, H. (2002) Enzyme catalysis in organic synthesis, VCH
8. Kazlauskas R.J., Bornscheuer U.T. Biotransformations with lipases. Rehm H.J., et al. Biotechnology. 8a:1998;37-191 Wiley-VCH.
9. Bornscheuer U.T. Microbial carboxyl esterases - classification, properties and application in biocatalysis. FEMS Microbiol. Rev. 26:2002;73-81.
10. Verger R. Interfacial activation' of lipases: Facts and artefacts. Trends Biotechnol. 15:1997;32-38.
11. Ollis D.L., et al. The α/β hydrolase fold. Protein Eng. 5:1992;197-211.
12. Pleiss J., et al. Lipase engineering database: Understanding and exploiting sequence-structure-function relationships. J. Mol. Catal. B Enzym. 10:2000;491-508.
13. Huge-Jensen B., et al. Rhizomucor miehei triglyceride lipase is processed and secreted from transformed Aspergillus oryzae. Lipids. 24:1989;781-785.
14. Schmidt-Dannert C., Arnold F.H. Directed evolution of industrial enzymes. Trends Biotechnol. 17:1999;135-136.
15. Brocca S., et al. Design, total synthesis, and functional overexpression of the Candida rugosa lip1 gene encoding for a major industrial lipase. Protein Sci. 7:1998;1415-1422.
16. Khmelnitsky Y.L., et al. Engineering biocatalytic systems in organic media with low water content. Enzyme Microb. Technol. 10:1988;710-724.
17. Villeneuve P., et al. Customizing lipases for biocatalysis: A survey of chemical, physical and molecular biological approaches. J. Mol. Catal. B Enzym. 9:2000;113-148.
18. Balcao V.M., et al. Bioreactors with immobilized lipases: State of the art. Enzyme Microb. Technol. 18:1996;392-416.
19. Ivanov A.E., Schneider M.P. Methods for the immobilization of lipases and their use for ester synthesis. J. Mol. Catal. B Enzym. 3:1997;303-309.
20. Malcata F.X., et al. Immobilized lipase reactors for modification of fats and oils - a review. J. Am. Oil Chem. Soc. 67:1990;890-909.
21. Anderson E.M., et al. One biocatalyst - many applications: The use of Candida antarctica B-lipase in organic synthesis. Biocatal. Biotransform. 16:1998;181-204.
22. Lalonde J.J., et al. Cross-linked crystals of Candida rugosa lipase: Highly efficient catalysts for the resolution of chiral esters. J. Am. Chem. Soc. 117:1995;6845-6852.
23. Collins A.M., et al. Scale-up of a chiral resolution using cross-linked enzyme crystals. Org. Process Res. Dev. 2:1998;400-406.
24. Reetz M., et al. Efficient heterogeneous biocatalysts by entrapment of lipases in hydrophobic sol-gel materials. Angew. Chem. Int. Ed. Engl. 34:1995;373-376.
25. Okahata Y., et al. A lipid-coated lipase as an enantioselective ester synthesis catalyst in homogeneous organic solvents. J. Org. Chem. 60:1995;2244-2250.
26. Tsuzuki W., et al. Preparation of organic-solvent-soluble enzyme (lipase B) and characterization by gel permeation chromatography. J Chem Soc [Perkin 1]. I:1991;1245-1247.
27. Laane C., et al. Rules for optimization of biocatalysis in organic solvents. Biotechnol. Bioeng. 30:1987;81-87.
28. Wasserscheid P., Keim W. Ionic liquids - new solutions for transition metal catalysis. Angew. Chem. Int. Ed. Engl. 39:2000;3772-3789.
29. Lau R.M., et al. Lipase-catalyzed reactions in ionic liquids. Org. Lett. 2:2000;4189-4192.
30. Schöfer, S.H. et al. (2001) Enzyme catalysis in ionic liquids: Lipase catalysed kinetic resolution of 1-phenylethanol with improved enantioselectivity. Chem. Comm. 425-426
31. Kim K-W., et al. Biocatalysis in ionic liquids: Markedly enhanced enantioselectivity of lipase. Org. Lett. 3:2001;1507-1509.
32. Park S., Kazlauskas R.J. Improved preparation and use of room-temperature ionic liquids in lipase-catalyzed enantio- and regioselective acylations. J. Org. Chem. 66:2002;8395-8401.
33. Halling P.J., et al. Relationsship between water activity and catalytic activity of lipases in organic media. Eur. J. Biochem. 222:1994;461-466.
34. Schmid U., et al. Highly selective synthesis of 1,3-oleoyl-2-palmitoylglycerol by lipase catalysis. Biotechnol. Bioeng. 64:1999;678-684.
35. Adlercreutz D., et al. Synthesis of phosphatidylcholine with defined fatty acid in the sn-1 position by lipase-catalyzed esterification and transesterification reaction. Biotechnol. Bioeng. 78:2002;403-411.
36. Kazlauskas R.J. Molecular modeling and biocatalysis: Explanations, predictions, limitations, and opportunities. Curr. Opin. Chem. Biol. 4:2000;81-88.
37. Harris J.L., Craik C.S. Engineering enzyme specificity. Curr. Opin. Chem. Biol. 2:1998;127-132.
38. Hæffner F., Norin T. Molecular modeling of lipase-catalyzed reactions. Prediction of enantioselectivities. Chem. Pharm. Bull. 47:1999;591-600.
39. Cedrone G., et al. Tailoring new enzyme functions by rational redesign. Curr. Opin. Struct. Biol. 10:2000;405-410.
40. Rotticci D., et al. Improved enantioselectivity of a lipase by rational protein engineering. Chembiochem. 2:2001;766-770.
41. Magnusson A., et al. Creation of an enantioselective hydrolase by engineered substrate-assisted catalysis. J. Am. Chem. Soc. 123:2001;4354-4355.
42. Schulz T., et al. Stereoselectivity of Pseudomonas cepacia lipase toward secondary alcohols: A quantitative model. Protein Sci. 9:2000;1053-1062.
43. Hwang B-Y., et al. Computer-aided molecular modeling of the enantioselectivity of Pseudomonas cepacia lipase toward γ- and δ-lactones. J. Mol. Catal. B Enzym. 10:2000;223-231.
44. Henke, E. et al. Activity of lipases and esterases towards tertiary alcohols: New insights into structure-function relationships. Angew. Chem. Int. Ed. Engl. (in press)
45. Cadwell R.C., Joyce G.F. Randomization of genes by PCR mutagenesis. PCR Methods Appl. 2:1992;28-33.
46. Stemmer W.P.C. Rapid evolution of a protein in vitro by DNA shuffling. Nature. 370:1994;389-391.
47. Bornscheuer U.T., Pohl M. Improved biocatalysts by directed evolution and rational protein design. Curr. Opin. Chem. Biol. 5:2001;137-142.
48. Schmidt-Dannert C. Directed evolution of proteins, metabolic pathways, and viruses. Biochemistry. 40:2001;13125-13136.
49. Wiseman A., et al. Novel biocatalytic enzymes by directed evolution. Trends Biotechnol. 19:2001;382.
50. Brakmann S. Brakmann S., Johnsson K., Directed molecular evolution of proteins. 2002;Wiley-VCH.
51. Wahler D., Reymond J-L. The adrenaline test for enzymes. Angew. Chem. Int. Ed. Engl. 41:2002;1229-1232.
52. Wahler D., et al. Enzyme fingerprints by fluorogenic and chromogenic substrate arrays. Angew. Chem. Int. Ed. Engl. 40:2001;4457-4460.
53. Badalassi F., et al. A versatile periodate coupled fluorogenic assay for hydrolytic enzymes. Angew. Chem. Int. Ed. Engl. 39:2000;4067-4070.
54. Baumann M., et al. A high-throughput-screening method for the identification of active and enantioselective hydrolases. Angew. Chem. Int. Ed. Engl. 40:2001;4201-4204.
55. Reetz M.T., et al. A method for high throughput screening of enantioselective catalysts. Angew. Chem. Int. Ed. Engl. 38:1999;1758-1761.
56. Bornscheuer U.T., et al. Directed evolution of an esterase for the stereoselective resolution of a key intermediate in the synthesis of epothilones. Biotechnol. Bioeng. 58:1998;554-559.
57. Henke E., Bornscheuer U.T. Directed evolution of an esterase from Pseudomonas fluorescens. Random mutagenesis by error-prone PCR or a mutator strain and identification of mutants showing enhanced enantioselectivity by resorufin-based fluorescence assay. Biol. Chem. 380:1999;1029-1033.
58. Liebeton K., et al. Directed evolution of an enantioselective lipase. Chem. Biol. 7:2000;709-718.
59. Reetz M.T., et al. Creation of enantioselective biocatalysts for organic chemistry by in vitro evolution. Angew. Chem. Int. Ed. Engl. 36:1997;2830-2832.
60. Reetz M.T., et al. Directed evolution of an enantioselective enzyme through combinatorial multiple-cassette mutagenesis. Angew. Chem. Int. Ed. Engl. 40:2001;3589-3591.
61. Kauffmann I., Schmidt-Dannert C. Conversion of Bacillus thermocatenulatus lipase into an efficient phospholipase with increased activity towards long-chain fatty acyl substrates by directed evolution and rational design. Protein Eng. 14:2001;919-928.
62. van Kampen M.D., Egmond M.R. Directed evolution: From a staphylococcal lipase to a phospholipase. Eur. J. Lipid Sci. Technol. 102:2000;717-726.