Stereoselective lipases from Burkholderia sp., cloning and their application to preparation of methyl (R)-N-(2,6-dimethylphenyl)alaninate, a key intermediate for (R)-Metalaxyl

Journal of Biotechnology

Volumn 120, Issue 2, 2005, Pages 174-182

  Park, Oh Jin ^a   Lee, Sang Hyun ^a  

^a LG Chemical Ltd   (South Korea)

Author keywords

(R) Metalaxyl; Burkholderia; Enzymes; Hydrolytic kinetic resolution; Lipases

Indexed keywords

ALCOHOLS; DNA; FUNGICIDES; MICROORGANISMS; MOLECULAR WEIGHT; STEREOCHEMISTRY;

(R)-METALAXYL; BURKHOLDERIA; HYDROLYTIC KINETIC RESOLUTION; LIPASES;

ENZYMES;

2 PROPANOL; ALANINE DERIVATIVE; METALAXYL; N (2,6 DIMETHYLPHENYL)ALANINATE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; BURKHOLDERIA; DNA SEQUENCE; MOLECULAR CLONING; MOLECULAR WEIGHT; NONHUMAN; NUCLEOTIDE SEQUENCE; PRECIPITATION; PRIORITY JOURNAL; SOIL; STEREOCHEMISTRY; SYNTHESIS;

ALANINE; AMINO ACID SEQUENCE; BASE SEQUENCE; BIOTECHNOLOGY; BURKHOLDERIA; CLONING, MOLECULAR; DNA, BACTERIAL; FUNGICIDES, INDUSTRIAL; GENES, BACTERIAL; LIPASE; MOLECULAR SEQUENCE DATA; SEQUENCE HOMOLOGY, AMINO ACID;

BURKHOLDERIA; BURKHOLDERIA SP.;

EID: 26444540723     PISSN: 01681656     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jbiotec.2005.06.026     Document Type: Article

References (35)

1. S. Altschul, L. Madden, A. Schaeffer, J. Zhang, Z. Zhang, W. Miller, and D.J. Lipman Gapped BLAST and PSI-BLAST: a new generation of protein database search program Nucleic Acids Res. 25 1997 3389 3402
2. S. Aoyama, N. Yoshida, and S. Inouye Cloning, sequencing, and expression and nucleotide sequence of the lipase from Pseudomonas fragi IFO-12049 in E. coli FEBS Lett. 242 1988 36 40
3. J.L. Arpigny, and K.-E. Jaeger Bacterial lipolytic enzymes: classification and properties Biochem. J. 343 1999 177 183
4. F. Balkenhol, K. Ditrich, B. Hauer, and W. Ladner Optically active amines via lipase-catalyzed methoxyacetylation J. Prakt. Chem. 339 1997 381 384
5. F. Beisson, A. Tiss, C. Rivière, and R. Verger Methods for lipase detection and assay: a critical review Eur. J. Lipid Sci. Technol. 102 2000 133 153
6. U. Bornscheuer, O.W. Reif, R. Lausch, R. Freitag, T. Scheper, F.N. Kolisis, and U. Menge Lipase of Pseudomonas cepacia for biotechnological purposes: purification, crystallization and characterization Biochim. Biophys. Acta 1201 1994 55 60
7. U.T. Bornscheuer, and R.J. Kazlauskas Hydrolases in Organic Synthesis: Regio- and Stereoselective Biotransformations 1999 Wiley-VCH Weinheim
8. C.S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih Quantitative analysis of biochemical kinetic resolutions of enantiomers J. Am. Chem. Soc. 104 1982 7294 7299
9. Y. Chikusa, Y. Hirayama, M. Ikunaka, T. Inoue, S. Kamiyama, M. Moriwaki, Y. Nishimoto, F. Nomoto, K. Ogawa, T. Ohno, K. Otsuka, A.K. Sakota, N. Shirasaka, A. Uzura, and K. Uzura There's no industrial biocatalyst like hydrolase: development of scalable enantioselective processes using hydrolytic enzymes Org. Process Res. Dev. 7 2003 289 296
10. F. Effenberger, U. Burkhard, and J. Willfahrt Enantioselekive synthese N-substituierter a-amino carbonsauren aus a-hydroxycarbonsauren Liebig. Ann. Chem. 1986 314 333
11. L.G. Frenken, M.R. Egmond, A.M. Batenburg, J.W. Bos, C. Visser, and C.T. Verrips Cloning of the Pseudomonas glumae lipase gene and determination of the active site residues Appl. Environ. Microbiol. 58 1992 3787 3791
12. M. Fischer, and J. Pleiss The lipase engineering database: a navigation and analysis tool for protein families Nucleic Acid Res. 31 2003 319 321
13. A.W. Garrison Issues on the enantioselectivity of chiral agrochemicals Chim. Oggi. 20 2002 28 32
14. R.A. Gross, B. Kalra, and A. Kumar Polyester and polycarbonate synthesis by in vitro enzyme catalysis Appl. Microbiol. Biotechnol. 55 2001 655 660
15. T. Izumi, K. Nakamura, Y. Shimada, A. Sugihara, Y. Tomonaga, and T. Fukase Cloning, nucleotide sequencing, and expression in Escherichia coli of a lipase and its activator gene from Pseudomonas sp. KWI-56 Agric. Biol. Chem. 55 1991 2349 2357
16. K.-E. Jaeger, and M.T. Reetz Microbial lipases form versatile tools for biotechnology Trends Biotechnol. 16 1998 396 403
17. K.-E. Jaeger, B.W. Dijkstra, and M.T. Reetz Bacterial biocatalysts: molecular biology, three-dimensional structures, and biotechnological applications of lipases Annu. Rev. Microbiol. 53 1999 315 351
18. S. Jorgensen, K.W. Skov, and B. Diderichsen Cloning, sequence, and expression of a lipase gene from Pseudomonas cepacia: lipase production in heterologous hosts requires two Pseudomonas genes J. Bacteriol. 173 1991 559 567
19. K.-E. Jaeger, T. Eggert, A. Eipper, and M.T. Reetz Directed evolution and the creation of enantioselective biocatalysts Appl. Microbiol. Biotechnol 55 2001 519 530
20. M. Kordel, B. Hofmann, D. Schomburg, and R.D. Schmid Extracellular lipase of Pseudomonas sp. strain ATCC 21808: purification, characterization, crystallization, and preliminary X-ray diffraction data J. Bacteriol. 173 1991 4836 4841
21. D. Lang, B. Hofmann, L. Haalck, H.-J. Hecht, F. Spener, R.D. Schmid, and D. Schromburg Crystal structure of a bacterial lipase from Chromobacterium viscosum ATCC 6918 refined at 1.6 angstroms resolution Mol. Biol. 259 1996 704 717
22. A. Liese, K. Seelbach, and C. Wandrey Industrial Biotransformations 2000 Wiley-VCH Weinheim
23. D. Litthauer, A. Ginster, and E.E. Skein Pseudomonas luteola lipase: a new member of the 320-residue Pseudomonas lipase family Enzyme Microb. Technol. 30 2002 209 215
24. C.A. Martinez, D.R. Yazbeck, and J. Tao An efficient enzymatic preparation of rhinovirus protease inhibitor intermediates Tetrahedron: Asymmetry 60 2004 759 764
25. Nakanishi, J., Kurono, Y., Koide, Y., Beppu, T., 1989. Recombinant DNA, bacterium of the genus Pseudomonas containing it, and process for preparing lipase using it. European Patent 0,331,376 (issued to Amano Phamaceutical Co.).
26. O.-J. Park, S.-H. Lee, T.-Y. Park, S.-W. Lee, and K.-H. Cho Enzyme-catalyzed preparation of methyl (R)-N-(2,6-dimethylphenyl)alaninate, a key intermediate for (R)-Metalaxyl Tetrahedron: Asymmetry 16 2005 1221 1225
27. R.N. Patel, A. Banergee, R.Y. Ko, J.M. Howell, W.S. Li, F.T. Comezoglu, R.A. Partyka, and L. Szarka Enzymic preparation of (3R-cis)-3-(acetyloxy)-4- phenyl-2-azetidinone: a taxol side-chain synthon Biotechnol. Appl. Biochem. 20 1994 23 33
28. M.T. Reetz, S. Wilensek, D. Zha, and K.-E. Jaeger Directed evolution of an enantioselective enzyme through combinatorial multiple-cassette mutagenesis Angew. Chem. Int. Ed. Engl. 40 2001 3589 3591
29. M.T. Reetz Lipases as practical biocatalysts Curr. Opin. Chem. Biol. 6 2002 145 150
30. M.T. Reetz Controlling the enantioselectivity of enzymes by directed evolution: Practical and theoretical ramifications Proc. Natl. Acad. Sci. 101 2004 5716 5722
31. F. Rosenau, and K.-E. Jaeger Bacterial lipases from Pseudomonas: regulation of gene expression and mechanisms of secretion Biochimie 82 2000 1 10
32. F. Roseenau, J. Tommassen, and K.-E. Jaeger Lipase-specific foldases Chem. BioChem. 5 2004 152 161
33. A.J.J. Straathof, S. Panke, and A. Schmid The production of fine chemicals by biotransformations Curr. Opin. Biotechnol. 13 2002 548 556
34. J.D. Thompson, D.G. Higgins, and T.J. Gibson CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice Nucleic Acids Res. 22 1994 4673 4680
35. D.R. Yazbeck, J. Tao, C.A. Martinez, B.J. Kline, and S. Hu Automated enzyme screening methods for the preparation of enantiopure pharmaceutical intermediates Adv. Synth. Catal. 345 2003 524 532