Asymmetric reduction of α, β-unsaturated ketone to (R) allylic alcohol by Candida chilensis

Biotechnology and Bioengineering

Volumn 93, Issue 4, 2006, Pages 674-686

  Pollard, D J ^a   Telari, K ^a   Lane, J ^a   Humphrey, G ^a   McWilliams, C ^a   Nidositko, S ^a   Salmon, P ^a   Moore, J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Alpha beta unsaturated ketone; Candida chilensis; Whole cell reduction

Indexed keywords

ALCOHOLS; COMPOSITION; ENZYMES; FERMENTATION; OPTIMIZATION; PATIENT TREATMENT; STATISTICAL METHODS; TOXICITY;

ALPHA-BETA UNSATURATED KETONE; CANDIDA CHILENSIS; WHOLE CELL REDUCTION;

KETONES;

ALCOHOL; ALLYL COMPOUND; KETONE;

ARTICLE; BIOTRANSFORMATION; CANDIDA; CELL GROWTH; CELL STRUCTURE; CENTRIFUGATION; CHEMICAL REACTION; ENANTIOMER; ENZYME ACTIVITY; FERMENTATION; MICROBIAL BIOMASS; NONHUMAN; PH; STEREOCHEMISTRY; TEMPERATURE; VOLUMETRY;

BIOTRANSFORMATION; CANDIDA; FERMENTATION; HEPTANOL; INDUSTRIAL MICROBIOLOGY; INTEGRIN ALPHAVBETA3; KETONES; OXIDATION-REDUCTION; PILOT PROJECTS; PROPANOLS; STEREOISOMERISM;

CANDIDA; CANDIDA CHILENSIS;

EID: 33644889382     PISSN: 00063592     EISSN: 10970290     Source Type: Journal    
DOI: 10.1002/bit.20751     Document Type: Article

References (24)

1. Chartrain M, Greasham R, Moore J, Reider P, Robinson D, Buckland B. 2001. Asymmetric bioreductions: Applications to the synthesis of pharmaceuticals. J Mol Cat B 11:503-512.
2. Cockshott AR, Sullivan GR. 2001. Improving the fermentation for Echinocandin B production. Part I: Sequential statistical experimental design. Process Biochem 36:647-660.
3. 3 antagonists for the prevention and treatment of osteoporosis. J Med Chem 47:4829-4837.
4. D'Arrigo P, Lattanzio M, Pedrocchi Fantoni G, Servi S. 1998. Chemoenzymatic synthesis of the active enantiomer of the anoressant 2-benzylmorpholine. Tetrahedron Asym 9:4021-4026.
5. Erciyas E, Erkaleli I, Cosar G. 1994. Antimicrobial evaluation of some styryl ketone derivatives and related thiol adducts. J Pharma Sci 83:545-548.
6. Forni A, Moretti I, Prati F, Torre G. 1994. Stereochemical control in yeast reduction of fluorinated β-diketones. Tetrahedron 50:11995-12000.
7. Fronza G, Fogliato C, Fuganti C, Lanati S, Rallo R, Servi S. 1995. On the mode of baker's yeast reduction of benzylidenecyclohexanone. Tetrahedron Lett 36:123-124.
8. Greasham R, Herber W. 1996. Design and optimization of growth media. In: Rhodes PM, Stanbury PF, (editors). Applied microbial physiology - A practical approach. Oxford: Oxford University Press, pp 53-74.
9. Grinbergs J, Yarrow D. 1970. Two new Candida species: Candida chilensis sp. N. and Candida valdiviana sp. N. Antonie van Leeuwenhoek 36:143-148.
10. Hage A, Petra DGI, Field JA, Schipper D, Wijnberg J, Kamer P, van Leeu wen P, Wever R, Schoemaker H. 2001. Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: Complementary approaches. Tetrahedon Asym 12:1025-1034.
11. Hayakawa R, Nozawa K, Shimizu M, Fujisawa T. 1998. Control of enantioselectivity in the bakers yeast reduction of β-keto ester derivatives in the presence of sulfur compound. Tetra Lett 39:67-70.
12. Homann M, Vail RB, Previte E, Tamarez M, Morgan B, Dodds D, Zaks A. 2004. Rapid identification of enantioselective ketone reductions using targeted microbial libraries. Tetrahedron 60:789-797.
13. Junker B, Seeley A, Lester M, Kovatch M, Schmitt J, Boryscwicz S, Lynch J, Zhang J, Greasham R. 2002. Use of frozen bagged seed inoculum for secondary metabolite and bioconversion processes at the pilot scale. Biotechnol Bioeng 79:628-640.
14. Kawai Y, Saitou K, Hida K, Dao DH, Ohno A. 1996. Stereochemical control in microbial reduction. Bull Chem Soc Jpn 69:2633-2638.
15. Kizaki N, Yasohara Y, Hasegawa J, Wada M, Kataoka M, Shimizu S. 2001. Synthesis of optically pure ethyl (S)-4-chloro-3-hydroxybutanoate by Escherichia coli transformant cells coexpressing the carbonyl reductase and glucose dehydrogenase genes. Appl Microbiol Biotechnol 55:590-595.
16. Koul S, Crout DHG, Errington W, Tax J. 1995. Biotransformation of α β unsaturated carbonyl compounds: Sulfides, sulfoxides, sulfones, nitriles and esters by yeast species: Carbonyl group and carbon-carbon double bond reduction. J Chem Soc Perkin Trans 2969-2988.
17. Lye G, Woodley J. 1999. Application of in situ product-removal techniques to biocatalytic processes. Trends in Biotech 17:395-402.
18. Nakamura K, Yamanaka R, Matsuda T, Harada T. 2003. Recent developments in asymmetric reduction of ketones with biocatalysts. Tetrahedron Asym 14:2659-2681.
19. Pollard DJ, Hunt G, Kirschner T, Salmon PM. 2002a. Rheological characterization of a fungal fermentation for the production of pneumocandins. Bioprocess Biosyst Eng 24:373-383.
20. Pollard DJ, Kirscher TF, Hernandez D, Hunt G, Olewinski R, Salmon PM. 2002b. Pilot-scale process sensitivity studies for the scaleup of a fungal fermentation for the production of pneumocandins. Biotech Bioeng 78:270-279.
21. Stewart JD. 2000. Organic transformations catalyzed by engineered yeast cells and related systems. Curr Opinion in Biotech 11:363-368.
22. 3 receptor antagonists comprises culturing yeast microorganism in propagation medium and unsaturated ketone substrate. US20020187988; 12.12.2002.
23. Utaka M, Konishi S, Takeda A. 1986. Asymmetric reduction of Z-3-chloro-3-alken-2-ones with fermenting baker's yeast. Tetrahedron Lett 27:4737-4740.
24. Wang JC, Sakakibara M, Matsuda M, Itoh N. 1999. Site-directed mutagenesis of two zinc-binding centers of the NADH-dependent phenylacetaldehyde reductase from styrene-assimilating Corynebacterium sp strain ST-10. Biosci Biotech Biochem 63:2216-2218.