Synthesis of enantiopure (S)-2-hydroxyphenylbutanoic acid using novel hydroxy acid dehydrogenase from Enterobacter sp. BK2K

Biotechnology Progress

Volumn 23, Issue 3, 2007, Pages 606-612

  Cha, Minho ^a   Eun, Jung Kim ^a   Yun, Hyungdon ^b   Cho, Byung Kwan ^c   Kim, Byung Gee ^a  

^a Seoul National University   (South Korea)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^c UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COFACTORS; HYDROXY ACID DEHYDROGENASE;

CATALYSIS; ENZYME ACTIVITY; GENES; SYNTHESIS (CHEMICAL);

ORGANIC ACIDS;

2 HYDROXY 4 PHENYLBUTYRIC ACID; 2-HYDROXY-4-PHENYLBUTYRIC ACID; ALCOHOL DEHYDROGENASE; ARYLBUTYRIC ACID DERIVATIVE; D 2 HYDROXY ACID DEHYDROGENASE; D-2-HYDROXYACID DEHYDROGENASE; FORMATE DEHYDROGENASE; FORMATE DEHYDROGENASE (NADP+); UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; BIOLOGICAL MODEL; ENTEROBACTER; ENZYME SPECIFICITY; ENZYMOLOGY; GENETICS; METABOLISM; MOLECULAR GENETICS; PH; PROTEIN BINDING; SEQUENCE HOMOLOGY; STEREOISOMERISM; TEMPERATURE;

ALCOHOL OXIDOREDUCTASES; AMINO ACID SEQUENCE; ENTEROBACTER; FORMATE DEHYDROGENASES; HYDROGEN-ION CONCENTRATION; MODELS, BIOLOGICAL; MOLECULAR SEQUENCE DATA; PHENYLBUTYRATES; PROTEIN BINDING; SEQUENCE HOMOLOGY, AMINO ACID; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TEMPERATURE;

ENTEROBACTER; ENTEROBACTER SP.; ESCHERICHIA COLI;

EID: 34250374856     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp0602404     Document Type: Article

References (30)

1. Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; Wiley-VCH: Weinheim, 1997.
2. Groger, H. Enzymatic routes to enantiomerically pure aromatic α-hydroxy carboxylic acids: A further example for the diversity of biocatalysis. Adv. Synth. Catal. 2001, 343, 547-558.
3. Ojima, I. Catalytic Asymmetric Synthesis; Wiley-VCH: New York, 2000.
4. Adam, W.; Lazarus, M.; Saha-Moller, C. R.; Schreier, P. Biocatalytic synthesis of optically acitive α-oxyfunctionalized carboxyl compounds. Acc. Chem. Res. 1999, 32, 837-845.
5. Kamphuis, J.; Meijer; E. M.; Boesten; W. H. J.; Broxtermann, Q. B.; Kaptein, B.; Hermes, F. M.; Schoemaker, H. E. Production of natural, and synthetic L- and D-amino acids by aminopeptidases, and amino amidases. In Biocatalytic Production of Amino Acids and Derivatives; Rozzel, J. D., Wagner, W., Eds.; Hanser Publishers: New York, 1992; pp 177-206.
6. Fechter, M. H.; Griengl, H. In Enzyme Catalysis in Organic Synthesis, 2nd ed.; Drauz, K., Waldmann, H., Eds.; Wiley-VCH: Weinheim, 2002; Vol. 2, Chapter 14, p 974.
7. Effenberger, F.; Bohme, J. Enzyme-catalysed enantioselective hydrolysis of racemic naproxen nitrile. Bioorg. Med. Chem. 1994, 2 (7), 715-721.
8. Osprian, I.; Fechter, M. H.; Griengl, H. Biocatalytic hydrolysis of cyanohydrins: an efficient approach to enantiopure α-hydroxy carboxylic acids. J. Mol. Catal. B: Enzym. 2003, 24-25, 89-98.
9. Layh, N.; Stolz, A.; Bohme, J.; Effenberger, F.; Knackmuss, H.-J. Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates. J. Biotechnol. 1994, 33 (2), 175-182.
10. Kalaritis, P.; Regenye, R. W.; Partridge, J. J.; Coffen, D. L. Kinetic resolution of 2-substituted esters catalyzed by a lipase ex. Pseudomonas fluoresces. J. Org. Chem. 1990, 55, 812-815.
11. Liese, A.; Kragl, U.; Kierkels, H.; Schulze, B. Membrane reactor development for the kinetic resolution of ethyl 2-hydroxy-4-phenylbutyrate. Enzyme Microb. Technol. 2002, 30, 673-681.
12. Chadha, A.; Baskar, B. Biocatalytic deracemisation of α-hydroxy esters: high yield preparation of (S)-ethyl 2-hydroxy-4-phenylbutanoate from the racemate. Tetrahedron: Asymmetry 2002, 13, 1461-1464.
13. Glueck, S. M.; Larissegger-Schnell, B.; Csar, K.; Kroutil, W.; Faber, K. Biocatalytic racemisation of alpha-hydroxycarboxylic acids at physiological conditions. Chem. Commun. (Cambridge) 2005, (14), 1904-1905.
14. Glueck, S. M.; Pirker, M.; Nestl, B. M.; Ueberbacher, B. T.; Larissegger-Schnell, B.; Csar, K.; Hauer, B.; Stuermer, R.; Kroutil, W.; Faber, K. Biocatalytic racemization of aliphatic, arylaliphatic, and aromatic α-hydroxycarboxylic acids. J. Org. Chem. 2005, 70 (10), 4028-32.
15. Yun, H.; Choi, H. L.; Fadnavis, N. W.; Kim, B. G. Stereospecific synthesis of (R)-2-hydroxy carboxylic acids using recombinant E. coli BL21 overexpressing YiaE from Escherichia coli K12 and glucose dehydrogenase from Bacillus subtilis. Biotechnol Prog. 2005, 21, 366-71.
16. Yum, D.-Y.; Lee, B.-Y.; Hahm, D.-H.; Pan, J.-G. The yiaE gene, located at 80.1 minutes on the Escherichia coli chromosome, encodes a 2-ketoaldonate reductase. J. Bacteriol. 1998, 180, 5984-5988.
17. Fujita, Y.; Ramaley, R.; Freese, E. Location and properties of GDH in sporulating cells and spores of Bacillus subtilis. J. Bacteriol. 1977, 132, 282-293.
18. Cho, B.-K.; Seo, J.-H.; Kang, T.-W.; Kim, B.-G. Asymmetric synthesis of L-homophenylalanine by equilibrium-shift using recombinant aromatic L-amino acid transaminase. Biotechnol. Bioeng. 2003, 20, 83, 226-34.
19. Montemartini, M.; Santome, J. A.; Cazzulo, J. J.; Nowicki, C. Purification and partial structural and kinetic characterization of an aromatic L-alpha-hydroxy acid dehydrogenase from epimastigotes of Trypanosoma cruzi. Mol. Biochem. Parasitol. 1994, 68, 15-23.
20. Van der Donk, W. A.; Zhao, H. Recent developments in pyridine nucleotide regeneration. Curr. Opin. Biotechnol. 2003, 14, 421-426.
21. Kragl, U.; Vasic-Racki, D.; Wandrey, C. Continuous production of wert-leucine membrane reactors. Bioprocess Eng. 1996, 14, 291-297.
22. Hall, M. D.; Levitt, D. G.; Banaszak, L. J. Crystal structure of Escherichia coli malate dehydrogenase : A complex of the apoenzyme and citrate at 1.87 Å resolution. J. Mol. Biol. 1992, 226 (3), 867-882.
23. Kaluzna, I.; Andrew, A.; Bonilla, M.; Martzen, M. R.; Stewart, J. D. Enantioselective reductions of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae dehydrogenase. J. Mol. Catal. B: Enzym. 2002, 17, 101-105.
24. Goward, C. R.; Nicholls, D. J. Malate dehydrogenase: a model for structure, evolution, and catalysis. Protein Sci. 1994, 3, 1883-1888.
25. Eventoff, W.; Rossman, M. G.; Taylor, S. S.; Torff, H. J.;Meyer, H.; Keil, W.; Kiltz, H. H. Structural adaptations of lactate dehydrogenase isoenzymes. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 2677-2681.
26. Vernal, J.; Fiser, A.; Sali, A.; Müller, M.; Cazzulo, J. J.; Nowicki, C. Probing the specificity of a trypanosomal aromatic α-hydroxy acid dehydrogenase by site-directed mutagenesis. Biochem. Biophys. Res. Commun. 2002, 293, 633-639.
27. Xiao, M. T.; Huang, Y. Y.; Shi, X. A.; Guo, Y. H. Bioreduction of phenylglyoxylic acid to R-(-)-mandelic acid by Saccharomyces cerevisiae FD11b. Enzyme Microb. Technol. 2005, 37, 589-596.
28. Lee, J. H.; Choi, M. H.; Park, J. Y.; Kang, H. K.; Ryu, H. W.; Sunwo, C. S.; Wee, Y. J.; Park, K. D.; Kim, D. W.; Kim, D. M. Cloning and characterization of the lactate dehydrogenase genes from Lactobacillus sp. RKY2. Biotechnol. Bioprocess Eng. 2004, 9, 318-322.
29. Watanabe, K.; Hino, S.; Onodera, K.; Kajie, S.; Takahashi, N. Diversity in kinetics of bacterial phenol-oxygenating activity. J. Ferment. Bioeng. 1996, 81, 560-563.
30. Watanabe, K.; Teramoto, M.; Futamata, H.; Harayama, S. Molecular detection, isolation, and physiological characterization of functionally dominant phenol-degrading bacteria in activated sludge. Appl. Environ. Microbiol. 1998, 64, 4396-4402.