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

Biotechnology Progress

Volumn 21, Issue 2, 2005, Pages 366-371

  Yun, Hyungdon ^a   Choi, Hyeon Lok ^a   Fadnavis, Nitin W ^a   Kim, Byung Gee ^a  

^a Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CELLS; ENZYMES; ESCHERICHIA COLI; GENES; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

BACILLUS SUBTILIS; GLUCOSE DEHYDROGENASE; PHOSPHATE BUFFERS; STEREOSPECIFIC SYNTHESIS;

CARBOXYLIC ACIDS;

CARBOXYLIC ACID; ESCHERICHIA COLI PROTEIN; GLUCOSE DEHYDROGENASE; OXIDOREDUCTASE; PRIMER DNA; YIAE PROTEIN, E COLI;

ARTICLE; BACILLUS SUBTILIS; ENZYME SPECIFICITY; ENZYME STABILITY; ENZYMOLOGY; ESCHERICHIA COLI; GENETIC RECOMBINATION; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; NUCLEOTIDE SEQUENCE; SYNTHESIS;

BACILLUS SUBTILIS; BASE SEQUENCE; CARBOHYDRATE DEHYDROGENASES; CARBOXYLIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA PRIMERS; ENZYME STABILITY; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; GLUCOSE 1-DEHYDROGENASE; RECOMBINATION, GENETIC; SUBSTRATE SPECIFICITY;

BACILLUS SUBTILIS; ESCHERICHIA; ESCHERICHIA COLI; ESCHERICHIA COLI K12;

EID: 16344369425     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp049694w     Document Type: Article

References (31)

1. Coppola, G. M.; Schuster, H. F. α-Hydroxy Acids in Enantioselective Syntheses; Wiley-VCH: Weinheim, 1997.
2. Gröger, 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. Adam, W.; Lazarus, M.; Saha-Moller, C. R.; Schreier, P. Biocatalytic synthesis of optically active α-oxyfunctionalized carbonyl compounds. Acc. Chem. Res. 1999, 32, 837-845.
4. Chadha, A.; Manohar, M.; Soundararajan, T.; Lokeswari, T. S. Asymmetric reduction of 2-oxo-4-phenylbutanoic acid ethyl ester by Daucus carota cell cultures. Tetrahedron: Asymmetry 1996, 7, 1571-1572.
5. North, M. Synthesis and applications of nonracemic cyanohydrins. Tetrahedron: Asymmetry 2003, 14, 147-176.
6. 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.
7. Huang, S. H.; Tsai, S. W. Kinetic resolution of (R,S)-ethyl 2-hydroxyl-4-phenylbutyrate via lipase-catalyzed hydrolysis and transesterification in isooctane. J. Mol. Catal. B: Enzym. 2004, 28, 65-69.
8. 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.
9. 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.
10. Fadnavis, N. W.; Radhika, K.R.; Madhuri, K. V. Gelozymes' in organic synthesis. (Part 3): Lipase mediated synthesis of enantiomerically pure (R)- and (S)-enantiomers of 2-acetoxy-4-phenyl-(E)-but-3-enenitrile. Tetrahedron: Asymmetry 2004, 15, 549-553.
11. Schmidt, E.; Blaser, H. U.; Fauquex, P. F.; Sedelmeir, G.; Spindler, F. Microbial Reagents in Organic Synthesis; Servi, S., Ed.; Kluwer Academic Publishers: The Netherlands, 1992; pp 377.
12. Schummer, A.; Yu, H.; Simon, H. Polyfunctional (R)-2-hydroxycarboxylic acids by reduction of 2-oxo acids with hydrogen gas or formate and resting cells of Proteus vulgaris. Tetrahedron 1991, 47, 9019-9034.
13. Holbrook, J. J.; Willis, C. L.; Johnsen, K.; Hateley, M. J. Chiral synthesis of 2-hydroxy carboxylic acids with a dehydrogenase. U.S. Patent 6,033,882, 2000.
14. Chang, C. Y.; Yang, T. K. Asymmetric synthesis of ACE inhibitor Benazepril HCl via a bioreductive reaction. Tetrahedron: Asymmetry 2003, 14, 2239-2245.
15. Fujita, Y.; Ramaley, R.; Freese, E. Location and properties GDH in sporulating cells and spores of Bacillus subtilis. J. Bacteriol. 1977, 132, 282-293.
16. Stewart, J. D. Dehydrogenases and transaminases in asymmetric synthesis. Curr. Opin. Chem. Biol. 2001, 5, 120-129.
17. van der Donk, W. A.; Zhao, H. Recent developments in pyridine nucleotide regeneration. Curr. Opin. Biotechnol. 2003, 14, 421-426.
18. Bommarius, A. S.; Schwarm, M,; Drauz, K. Biocatalysis to amino acid-based chiral pharmaceuticals-examples and perspectives. J. Mol. Catal. B: Enzym. 1998, 5, 1-11.
19. Matsuyama, A.; Yamamoto, H.; Kobayashi, Y. Practical application of recombinant whole-cell biocatalysts for the manufacturing of pharmaceutical intermediates such as chiral alcohols. Org. Process Res. Dev. 2002, 6, 558-561.
20. Kataoka, M.; Kita, K.; Wada, M.; Yasohara, Y.; Hasegawa, J.; Shimizu, S. Novel bioreduction system for the production of chiral alcohols. Appl. Microbiol. Biotechnol. 2003, 62, 437-445.
21. 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.
22. Nunez, M. F.; Pellicer, M. T.; Badia, J.; Aguilar, J.; Baldoma, L. Biochemical characterization of the 2-ketoacid reductases encoded by ycdW and yiaE genes in Escherichia coli. Biochem. J. 2001, 354, 707-715.
23. +-specific formate dehydrogenases. Biotechnol. Bioeng. 1999, 64, 187-193.
24. Boonstra, B.; Rathbone, D. A.; French, C. E.; Walker, E. H.; Bruce, N. C. Cofactor regeneration by a soluble pyridine nucleotide transhydrogenase for biological production of hydromorphone. Appl. Environ. Microbiol. 2000, 66, 5161-5166.
25. Hummel W. Large-scale applications of NAD(P)-dependent oxidoreductases: recent developments. TIBTECH 1999, 17, 487-492.
26. Lampel K. A.; Uratani, B.; Chaudhry, G. R.; Ramaley, R. F.; Rudikoff, S. Characterization of the developmentally regulated Bacillus subtilis. J. Bacteriol. 1986, 166, 238-243.
27. Kaluzna, I.; Andrew, A. A.; Bonilla, M.; Martzen, M. R.; Stewart, J. D. Enantioselective reductions of ethyl 2-oxo-4-phenylbutyrate by Saccharomyces cerevisiae dehydrogenases. J. Mol. Catal. B: Enzym. 2002, 17, 101-105.
28. Dao, D. H.; Okamura, M.; Akasaka, T.; Kawai, Y.; Hida, K.; Ohno, A. Stereochemical control in microbial reduction. Part 31: Reduction of alkyl 2-oxo-4-arylbutyrates by baker's yeast under selected reaction conditions. Tetrahedron: Asymmetry 1998, 9, 2725-2737.
29. Herold, P.; Indolese, A. F.; Studer, M.; Jalett, H. P.; Siegrist, U.; Blaser, H. U. New technical synthesis of ethyl (R)-2-hydroxy-4-phenylbutyrate of high enantiomeric purity. Tetrahedron 2000, 56, 6497.
30. Blaser, H. U.; Burkhardt, S.; Kirner, H. J.; Mossner, T.; Studer, M. Ethyl 2,4-Dioxo-4-phenylbutyrate: A Versatile Intermediate for the large-scale preparation of enantiomerically pure α-hydroxy and α-amino acid esters. Synthesis 2003, 1679-1682.
31. Drysdale, M. J.; Hind, S. L.; Jansen, M.; Reinhard, J. F., Jr. Synthesis and SAR of 4-aryl-2-hydroxy-4-oxobut-2-enoic acids and esters and 2-amino-4-aryl-4-oxobut-2-enoic acids and esters: Potent inhibitors of Kynurenine-3-hydroxylase as potential neuroprotective agents. J. Med. Chem. 2000, 43, 123-127.