Equilibrium-dependent hydration of ethyl 4,4,4-trifluoro-acetoacetate in aqueous solutions and consequences for the whole-cell biotransformation with Saccharomyces cerevisiae

Enzyme and Microbial Technology

Volumn 32, Issue 3-4, 2003, Pages 491-497

  Bertau, Martin ^a   Scheller, Dieter ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Baker's yeast; Bioemulsification; Biotransformation; Enantioselective synthesis; Ethyl 4,4,4 trifluoro acetoacetate; NMR

Indexed keywords

BIOCONVERSION; CHEMICAL REACTIONS; HYDRATION; SOLVENTS;

BIOTRANSFORMATION;

AROMATIC COMPOUNDS;

4,4,4 TRIFLUOROACETOACETATE; ACETIC ACID DERIVATIVE; EMULSIFYING AGENT; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BIOAVAILABILITY; BIOTRANSFORMATION; CONTROLLED STUDY; ENANTIOSELECTIVITY; FERMENTATION; HYDRATION; MICROORGANISM; NONHUMAN; PH; POPLITEAL CYST; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; TEMPERATURE;

SACCHAROMYCES; SACCHAROMYCES CEREVISIAE;

EID: 0037416702     PISSN: 01410229     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0141-0229(02)00341-1     Document Type: Article

References (28)

1. Götzö SP, Seebach D, Sanglier JJ. EPC syntheses of trifluorocitronellol and of hexafluoropyrenophorin - a comparison of their physiological properties with the nonfluorinated analogs. Eur J Org Chem 1999;2533-44.
2. Bertau M., Bürli M., Wagner P., Hungerbühler E. A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones. Tetrahedron: Asymmetry. 12:2001;2303-2307.
3. Rabasseda X., Sorbera L.A., Castaner J. Befloxatone. Drugs Fut. 24:1999;1057-1067.
4. Tixidre A., Zard L., Rossey G., Bourbon A. Procede de preparation enzymatique d'un intermediaire de synthese de la befloxatone. EP 0736606. Chem. Abstr. 125:1996;273719.
5. Jegham S., Puech F., Burnier P., Berthon D., Leclerc O. Preparation of oxazolidin-2-one derivatives as monoamine oxidase inhibitors. WO 9713768. Chem. Abstr. 126:1996;330609.
6. Seebach D., Renaud P., Schweizer W.B., Zueger M.F., Brienne M.J. Selective inhibition of R-enzymes by simple organic acids in yeast-catalysed reduction of ethyl 3-oxobutanoate. Helv. Chim. Acta. 67:1984;1843-1853.
7. Bucciarelli M., Forni A., Moretti I., Prati F., Torre G. Substituent effect on the absolute stereochemistry of the asymmetric reduction of fluorine-containing β-diketones by bakers' yeast. Biocatalysis. 9:1994;313-320.
8. Bertau M. Novel unusual microbial dehalogenation during enantioselective reduction of ethyl 4,4,4-trifluoro acetoacetate with Baker's yeast. Tetrahedron Lett. 42:2001;1267-1268.
9. Antolini L., Forni A., Davoli P., Moretti I., Prati F. Stereoselective synthesis and absolute configuration of (1′R,3R,4R)-4-acetoxy-3-(2′,2′,2′,-trifluoro- 1′-hydroxyethyl)-azetidin-2-one. Tetrahedron: Asymmetry. 9:1998;285-292.
10. Davoli P., Forni A., Moretti I., Prati F., Torre G. (R)-(1) and (S)-(2) ethyl 4,4,4-trifluoro-3-hydroxy butanoate by enantioselective Baker's yeast reduction. Enzyme Microb. Technol. 25:1999;149-152.
11. Schwetlick K. Organikum, 21, ed. Weinheim: Wiley/VCH; 2001. p. 747.
12. Gambaryan N.P., Rokhlin E.M., Zeifman Y.V., Ching-Yun C., Knunyants I.L. Reaktionen der Carbonylgruppe fluorierter Ketone. Angew. Chem. 78:1966;1008-17;
13. Gambaryan N.P., Rokhlin E.M., Zeifman Y.V., Ching-Yun C., Knunyants I.L. Reaktionen der Carbonylgruppe fluorierter Ketone. Angew. Chem. Int. Ed. 5:1966;947-956.
14. Angelova B., Schmauder H.P. Lipophilic compounds in biotechnology - interactions with cells and technological problems. J. Biotechnol. 67:1999;13.
15. Rosenberg E., Ron E.Z. Bioemulsans: microbial polymeric emulsifiers. Curr. Opin. Biotechnol. 8:1997;313-316.
16. Barriga J.A.T., Cooper D.T., Idziak E.S., Cameron D.R. Components of the bioemulsifier from S. cerevisiae. Enzyme Microb. Technol. 25:1999;96-102.
17. Funderburk L.H., Aldwin L., Jencks W.P. Mechanisms of general acid and base catalysis of the reactions of water and alcohols with formaldehyde. J. Am. Chem. Soc. 100:1978;5444-5459.
18. Cimprich P., Slavik J. Fluorescence measurement of intracellular pH of the yeast Saccharomyces cerevisiae. Folia Microbiol. (Praha). 41:1996;84.
19. Cimprich P., Slavik J., Kotyk A. Distribution of individual cytoplasmic pH values in a population of the yeast Saccharomyces cerevisiae. FEMS Microbiol. Lett. 130:1995;245-252.
20. Ohta H., Kobayashi N., Sugai T. Reduction of acyl enolates of α-substituted β-keto esters by Bakers' yeast. Agric. Biol. Chem. 54:1990;489-493.
21. Santaniello E, Ferraboschi P, Grisenti P, Aragozzini F, Maconi E. A biocatalytic approach to the enantioselective synthesis of (R)- and (S)-malic acid. J Chem Soc, Perkin Trans I 1991;601-5.
22. von Arx M., Mallat T., Baiker A. First enantioselective hydrogenation of a trifluoro-β-keto ester with cinchona-modified platinum. J. Catal. 193:2000;161-164.
23. Fernandez R., Martin-Zamora E., Pareja C., Vazquez J., Diez E., Monge A.et al. Synthese von enantiomerenreinen α-alkoxy-α-trifluuormethylaldehyden und -carbonsäuren aus Trifluormethylketonen. Angew. Chem. 110:1998;3400-598;
24. Fernandez R., Martin-Zamora E., Pareja C., Vazquez J., Diez E., Monge A.et al. Synthese von enantiomerenreinen α-alkoxy-α-trifluuormethylaldehyden und -carbonsäuren aus Trifluormethylketonen. Angew. Chem. Int. Ed. 37:1998;3428-3430.
25. Yamazaki T., Okamura N., Kitazume T. Stereoselective preparation of ethyl 2,3-dihydroxy-4,4,4-trifluorobutyrates via enzymatic optical resolution. Tetrahedron: Asymmetry. 1:1990;521-524.
26. Yamazaki T., Asai M., Ohnogi T., Lin J.T., Kitazume T. Microbial approaches to optically active sulfur-containing fluorinated compounds. J. Fluorine Chem. 35:1987;537-553.
27. Kitazume T, Ishikawa N. Introduction of center of chirality into fluorocompounds by microbial transformation of 2,2,2-trifluorethanol. Chem Lett 1984;1815-8.
28. Bucciarelli M, Forni A, Moretti I, Torre G. Asymmetric reduction of trifluoromethyl and methyl ketones by yeast; an improved method. Synthesis 1983;897-9.