Substrate inhibition and product degradation during the reduction of 4-oxoisophorone by Saccharomyces cerevisiae

Enzyme and Microbial Technology

Volumn 37, Issue 6, 2005, Pages 625-633

  Buque Taboada, Evelyn M ^a,b   Straathof, Adrie J J ^a   Heijnen, Joseph J ^a   Van Der Wielen, Luuk A M ^a,b  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b UNIVERSITY OF SAN CARLOS   (Philippines)

Author keywords

4 Oxoisophorone; Baker's yeast; Inhibition; Kinetics; Levodione; Reduction

Indexed keywords

CATALYSTS; CELLS; KETONES; SYNTHESIS (CHEMICAL); YEAST;

4-OXOISOPHORONE; BAKER'S YEAST; INHIBITION; KINETICS; LEVODIONE; REDUCTION;

REDUCTION;

4 OXOISOPHORONE; ACTINOL; ALCOHOL DERIVATIVE; ISOPHORONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CONTROLLED STUDY; DEGRADATION; ENZYME KINETICS; ENZYME SUBSTRATE; NONHUMAN; REDUCTION; SACCHAROMYCES CEREVISIAE; YEAST CELL;

SACCHAROMYCES CEREVISIAE;

EID: 24944503111     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.enzmictec.2005.04.019     Document Type: Article

References (22)

1. H.G.W. Leuenberger, W. Boguth, E. Widmer, and R. Zell Synthesis of optically active natural carotenoids and structurally related compounds. I. Synthesis of the chiral key compound (4R,6R)-4-hydroxy-2,2,6- trimethylcyclohexanone Helv Chim Acta 59 1976 1832 1849
2. H. Mayer Synthesis of optically active carotenoids and related compounds Pure Appl Chem 51 1979 535 564
3. N. Hori, T. Hieda, and Y. Mikami Microbial conversion of 4-oxoisophorone by thermophile Thermomonospora curvata Agric Biol Chem 48 1984 123 129
4. K. Sode, K. Kajiwara, E. Tamiya, and I. Karube Continuous asymmetric reduction of 4-oxoisophorone by thermophilic bacteria using a hollow fiber reactor Biocatalysis 1 1987 77 86
5. M. Von Arx, T. Mallat, and A. Baiker Unprecedented selectivity behaviour in the hydrogenation of an α,β-unsaturated ketone: hydrogenation of ketoisophorone over Almunia-supported Pt and Pd J Mol Catal A 148 1999 275 283
6. 2 medium Ind Eng Chem Res 42 2003 6688 6696
7. E.M. Buque-Taboada, A.J.J. Straathof, J.J. Heijnen, and L.A.M. van der Wielen In-situ product removal using a crystallization loop in the asymmetric reduction of 4-oxoisophorone by Saccharomyces cerevisiae Biotechnol Bioeng 86 2004 795 800
8. HG.W. Leuenberger Microbiologically catalyzed reaction steps in the field of vitamin and carotenoid synthesis J. Tramper H.C. van der Plas P. Linko Biocatalysts in organic synthesis 1985 Elsevier Science Publishers Amsterdam 99 118
9. Fukuoka M, Hiraga K, Sekihara T. Microbial production of levodione. European Patent Application, EP 1074630A2, 2001.
10. Y. Yamazaki, Y. Hayashi, N. Hori, and Y. Mikami Microbial conversion of 4-oxoisophorone by Aspergillus niger Agric Biol Chem 52 1988 2919 2920
11. K. Sode, N. Hori, Y. Mikami, and I. Karobe Asymmetric reduction of 4-oxoisophorone using immobilized thermophilic bacteria under conditions of controlled cell growth Biocatalysis 2 1988 51 57
12. K. Nishii, K. Sode, and I. Karube Air-bubbling, hollow-fiber reactor with cell bleeding and cross-flow filtration Biotechnol Bioeng 35 1990 1155 1160
13. K. Nishii, K. Sode, and I. Karube Sequential two-step conversion of 4-oxoisophorone to 4-hydroxy-2,2,6-trimethylcyclohexanone by thermophilic bacteria Appl Microbiol Biotechnol 33 1990 245 250
14. K. Nishii, K. Sode, and I. Karube Continuous two-step bioconversion of 4-oxoisophorone to 4-hydroxy-2,2,6-trimethylcyclohexanone (4-HTMCH) by thermophilic bacteria Biotechnol Lett 17 1995 785 790
15. P. Wanner, and R. Tressl Purification and characterization of two enone reductases from Saccharomyces cerevisiae Eur J Biochem 255 1998 271 278
16. M. Kataoka, A. Kotaka, A. Hasegawa, M. Wada, A. Yoshizumi, and S. Nakamori Old yellow enzyme from Candida macedoniensis catalyses the stereospecific reduction of the CC bond of ketoisophorone Biosci Biotechnol Biochem 66 2002 2651 2657
17. M. Wada, A. Yoshizumi, S. Nakamori, and S. Shimizu Purification and characterization of monovalent cation-activated levodione reductase from Corynebacterium aquaticum M-13 Appl Environ Microbiol 65 1999 4399 4403
18. M. Wada, A. Yoshizumi, Y. Noda, M. Kataoka, S. Shimizu, and H. Takagi Production of a doubly chiral compound, (4R,6R)-4-hydroxy-2,2,6-trimethylcyclo- hexanone, by two-step enzymatic asymmetric reduction Appl Environ Microbiol 69 2003 933 937
19. A. Yoshisumi, M. Wada, H. Takagi, S. Shimizu, and S. Nakamori Cloning, sequence analysis, and expression in Escherichia coli of the gene encoding monovalent cation-activated levodione reductase from Corynebacterium aquaticum M-13 Biosci Biotechnol Biochem 65 2001 830 836
20. S. Sogabe, A. Yoshizumi, T.A. Fukami, Y. Shiratori, S. Shimizu, and H. Takagi The crystal structure and stereospecificity of levodione reductase from Corynebacterium aquaticum M-13 J Biol Chem 278 2003 19387 19395
21. E.M. Buque, I. Chin-Joe, Straathof AJJ, J.A. Jongejan, and J.J. Heijnen Immobilization affects the rate and enantioselectivity of 3-oxo ester reduction by baker's yeast Enzyme Microb Technol 31 2002 656 664
22. K. Han, and O. Levenspiel Extended Monod kinetics for substrate, product and cell inhibition Biotechnol Bioeng 32 1988 430 437