A new strategy to improve the efficiency and sustainability of Candida parapsilosis catalyzing deracemization of (R,S)-1-phenyl-1,2-ethanediol under non-growing conditions: Increase of NADPH availability

Journal of Microbiology and Biotechnology

Volumn 19, Issue 1, 2009, Pages 65-71

  Nie, Yao ^a   Yan, Xu ^a   Hu, Qing Sen ^a   Xiao, Rong ^b  

^a Key Laboratory of Industrial Biotechnology   (South Korea)

^b RUTGERS UNIVERSITY   (United States)

Author keywords

Candida parapsilosis; Deracemization; NADPH availability; Pentose; Sustainability

Indexed keywords

ARABINOSE; CHEMICAL COMPOUND; OXIDOREDUCTASE; PENTOSE PHOSPHATE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; RIBOSE; STYRENE GLYCOL; UNCLASSIFIED DRUG; XYLOSE; 6 AMINONICOTINAMIDE; ALCOHOL DEHYDROGENASE; ALCOHOL DEHYDROGENASE (NADP+); ALDEHYDE REDUCTASE; ETHYLENE GLYCOL DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; TERATOGENIC AGENT; XYLULOSE REDUCTASE;

ARTICLE; CANDIDA PARAPSILOSIS; CATALYSIS; CELL GROWTH; CELL METABOLISM; CELL REGENERATION; ENZYME ACTIVITY; FUNGAL CELL; NONHUMAN; OXIDATION REDUCTION REACTION; RACEMIZATION; BIOCATALYSIS; CANDIDA; DRUG EFFECT; ENZYMOLOGY; GROWTH, DEVELOPMENT AND AGING; METABOLISM; PENTOSE PHOSPHATE CYCLE;

CANDIDA PARAPSILOSIS;

6-AMINONICOTINAMIDE; ALCOHOL OXIDOREDUCTASES; ALDEHYDE REDUCTASE; ARABINOSE; BIOCATALYSIS; CANDIDA; D-XYLULOSE REDUCTASE; ETHYLENE GLYCOLS; NADP; OXIDATION-REDUCTION; PENTOSE PHOSPHATE PATHWAY; RIBOSE; TERATOGENS; XYLOSE;

EID: 63449108282     PISSN: 10177825     EISSN: 17388872     Source Type: Journal    
DOI: 10.4014/jmb.0804.283     Document Type: Article

References (39)

1. Boonstra, B., D. A. Rathbone, C. E. French, E. H. Walker, and N. C. Bruce. 2000. Cofactor regeneration by a soluble pyridine nucleotide transhydrogenase for biological production of hydromorphone. Appl. Environ. Microbiol. 66: 5161-5166.
2. Bradford, M. M. 1976. A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72: 248-254.
3. Dahl, A. C. and J. O. Madsen. 1998. Baker's yeast: Production of D- and L-3-hydroxy esters. Tetrahedr. Asymm. 9: 4395-4417.
4. Gupte, S. A., T. Okada, I. F. McMurtry, and M. Oka. 2006. Role of pentose phosphate pathway-derived NADPH in hypoxic pulmonary vasoconstriction. Pulm. Pharmacol. Ther. 19: 303-309.
5. Haberland, J., A. Kriegesmann, E. Wolfram, W. Hummel, and A. Liese. 2002. Diastereoselective synthesis of optically active (2R,5R)-hexanediol. Appl. Microbiol. Biotechnol. 58: 595-599.
6. Ichinose, H., N. Kamiya, and M. Goto. 2005. Enzymatic redox cofactor regeneration in organic media: Functionalization and application of glycerol dehydrogenase and soluble transhydrogenase in reverse micelles. Biotechnol. Prog. 21: 1192-1197.
7. Ishige, T., K. Honda, and S. Shimizu. 2005. Whole organism biocatalysis. Curr. Opin. Chem. Biol. 9: 174-180.
8. Itoh, N., M. Matsuda, M. Mabuchi, T. Dairi, and J. Wang. 2002. Chiral alcohol production by NADH-dependent phenylacetaldehyde reductase coupled with in situ regeneration of NADH. Eur. J. Biochem. 269: 2394-2402.
9. Iwasaki, F., T. Maki, W. Nakashima, O. Onomura, and Y. Matsumura. 1999. Nonenzymatic kinetic resolution of 1,2-diols catalyzed by organotin compound. Org. Lett. 1: 969-972.
10. Jeffries, T. W. 2006. Engineering yeasts for xylose metabolism. Curr. Opin. Biotechnol. 17: 320-326.
11. Jeffries, T. W. and Y. S. Jin. 2004. Metabolic engineering for improved fermentation of pentoses by yeasts. Appl. Microbiol. Biotechnol. 63: 495-509.
12. Jiang, Q., S. Yao, and L. Mei. 2002. Tolerance of immobilized Baker's yeast in organic solvents. Enzyme Microb. Technol. 30: 721-725.
13. Karhumaa, K., R. Fromanger, B. Hahn-Hagerdal, and M. F. Gorwa-Grauslund. 2007. High activity of xylose reductase and xylitol dehydrogenase improves xylose fermentation by recombinant Saccharomyces cerevisiae. Appl. Microbiol. Biotechnol. 73: 1039-1046.
14. Kataoka, M., K. Kita, M. Wada, Y. Yasohara, J. Hasegawa, and S. Shimizu. 2003. Novel bioreduction system for the production of chiral alcohols. Appl. Microbiol. Biotechnol. 62: 437-445.
15. Kataoka, M., Y. Nomura, S. Shimizu, and H. Yamada. 1992. Enzymes involved in the NADPH regeneration system coupled with asymmetric reduction of carbonyl compounds in microorganisms. Biosci. Biotech. Biochem. 56: 820-821.
16. Koeller, K. M. and C. H. Wong. 2001. Enzymes for chemical synthesis. Nature 409: 232-240.
17. Kroutil, W., H. Mang, K. Edegger, and K. Faber. 2004. Recent advances in the biocatalytic reduction of ketones and oxidation of sec-alcohols. Curr. Opin. Chem. Biol. 8: 120-126.
18. Liese, A., M. Karutz, J. Kamphuis, C. Wandrey, and U. Kragl. 1996. Resolution of 1-phenyl-1,2-ethanediol by enantioselective oxidation overcoming product inhibition by continuous extraction. Biotechnol. Bioeng. 51: 544-550.
19. Lima, L. H. A., C. G. Pinheiro, L. M. P. de Moraes, S. M. de Freitas, and F. A. G. Torres. 2006. Xylitol dehydrogenase from Candida tropicalis: Molecular cloning of the gene and structural analysis of the protein. Appl. Microbiol. Biotechnol. 73: 631-639.
20. Lv, T., Y. Xu, X. Mu, and Y. Nie. 2007. Promotion effect of xylose co-substrate on stability of catalytic system for asymmetric redox of (R,S)-1-phenyl-1,2-ethanediol to its (S)-enantiomer by Candida parapsilosis. Chin. J. Catal. 28: 446-450.
21. Matsuyama, A., H. Yamamoto, N. Kawada, and Y. Kobayashi. 2001. Industrial production of (R)-1,3-butanediol by new biocatalysts. J. Mol. Catal. B Enzym. 11: 513-521.
22. Mertens, R., L. Greine, E. C. D. van den Ban, H. B. C. M. Haaker, and A. Liese. 2003. Practical applications of hydrogenase I from Pyrococcus furiosus for NADPH generation and regeneration. J. Mol. Catal. B Enzym. 24-25: 39-52.
23. Nakamura, K., Y. lnoue, and A. Ohno. 1995. Improvement of enantioselectivity of microbial reduction by using organic solvent redox coupler system. Tetrahedron. Lett. 36: 265-266.
24. Nie, Y., Y. Xu, and X. Q. Mu. 2004. Highly enantioselective conversion of racemic 1-phenyl-1,2-ethanediol by stereoinversion involving a novel cofactor-dependent oxidoreduction system of Candida parapsilosis CCTCC M203011. Org. Process Res. Dev. 8: 246-251.
25. Nie, Y., Y. Xu, X. Q. Mu, H. Y. Wang, M. Yang, and R. Xiao. 2007. Purification, characterization, gene cloning and expression of a novel alcohol dehydrogenase with anti-Prelog stereospecificity from Candida parapsilosis. Appl. Environ. Microbiol. 73: 3759-3764.
26. Panke, S., M. Held, and M. Wubbolts. 2004. Trends and innovations in industrial biocatalysis for the production of fine chemicals. Curr. Opin. Biotechnol. 15: 272-279.
27. Pitkanen, J. P., A. Aristidou, L. Salusjarvi, L. Ruohonen, and M. Penttila. 2003. Metabolic flux analysis of xylose metabolism in recombinant Saccharomyces cerevisiae using continuous culture. Metab. Eng. 5: 16-31.
28. Schmid, A., J. S. Dordick, B. Hauer, A. Kiener, M. Wubbolts, and B. Witholt. 2001. Industrial biocatalysis today and tomorrow. Nature 409: 258-268.
29. Schoemaker, H. E., D. Mink, and M. G. Wubbolts. 2003. Dispelling the myths-biocatalysis in industrial synthesis. Science 299: 1694-1697.
30. Strauss, U. T., U. Felfer, and K. Faber. 1999. Biocatalytic transformation of racemates into chiral building blocks in 100% chemical yield and 100% enantiomeric excess. Tetrahedr. Asymm. 10: 107-117.
31. Sultana, I., R. M. Mizanur, K. Takeshita, G. Takada, and K. Izumori. 2003. Direct production of D-arabinose from D-xylose by a coupling reaction using D-xylose isomerase, D-tagatose 3-epimerase and D-arabinose isomerase. J. Biosci. Bioeng. 95: 342-347.
32. Timasheff, S. N. 1993. The control of protein stability and association by weak interactions with water: How do solvents affect these processes? Annu. Rev. Biophys. Biomol. Struct. 22: 67-97.
33. +- specific formate dehydrogenases. Biotechnol. Bioeng. 64: 187-193.
34. Urlacher, V. B. and R. D. Schmid. 2006. Recent advances in oxygenase-catalyzed biotransformations. Curr. Opin. Chem. Biol. 10: 156-161.
35. van der Donk, W. A. and H. Zhao. 2003. Recent developments in pyridine nucleotide regeneration. Curr. Opin. Biotechnol. 14: 421-426.
36. Voss, C. V., C. C. Gruber, and W. Kroutil. 2008. Deracemization of secondary alcohols through a concurrent tandem biocatalytic oxidation and reduction. Angew. Chem. Int. Ed. Engl. 47: 741-745.
37. Walton, A. Z. and J. D. Stewart. 2002. An efficient enzymatic Baeyer-Villiger oxidation by engineered Escherichia coli cells under non-growing conditions. Biotechnol. Prog. 18: 262-268.
38. Yamamoto, H., A. Matsuyama, and Y. Kobayashi. 2002. Synthesis of ethyl (R)-4-chloro-3-hydroxybutanoate with recombinant Escherichia coli cells expressing (S)-specific secondary alcohol dehydrogenase. Biosci. Biotechnol. Biochem. 66: 481-483.
39. Zhang, Z., J. Yu, and R. C. Stanton. 2000. A method for determination of pyridine nucleotides using a single extract. Anal. Biochem. 285: 163-167.