Effects of cell stress protectant glutathione on the whole-cell biotransformation of ethyl 2-chloro-acetoacetate with Saccharomyces cerevisiae

Biocatalysis and Biotransformation

Volumn 23, Issue 1, 2005, Pages 9-17

  Jorg G ^a   Hemery T ^a   Bertau, Martin ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

Biotransformation; Dehalogenation; Glutathione; Stereoselective reduction; Xenobiotic stress

Indexed keywords

ACETONE; ALKYLATION; DEHALOGENATION; ENZYMES; HYDROLYSIS; REDUCTION;

BIOTRANSFORMATION; GLUTATHIONE; STEREOSELECTIVITY; XENOBIOTIC STRESS;

CELLS;

2 CHLOROACETOACETIC ACID ETHYL ESTER; ACETIC ACID ETHYL ESTER; ACETOACETIC ACID DERIVATIVE; CHLOROACETIC ACID; GLUTATHIONE; GLUTATHIONE TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; BIOTRANSFORMATION; CARBOHYDRATE ANALYSIS; CATALYST; CHEMICAL REACTION; CYTOSOLIC FRACTION; DEHALOGENATION; FLUORESCENCE ANALYSIS; GRAM POSITIVE BACTERIUM; HYDROLYSIS; IN VITRO STUDY; METHODOLOGY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; WHOLE CELL;

SACCHAROMYCES CEREVISIAE;

EID: 18444402208     PISSN: 10242422     EISSN: None     Source Type: Journal    
DOI: 10.1080/10242420500068231     Document Type: Article

References (36)

1. Ager DJ, Prakash I, Schaad DR. 1997. Chiral oxazolidinones in asymmetric synthesis. Aldrichim Acta 30:3-12.
2. N2 cyclization to oxazolidinones. Tetrahedron Lett 41:10071-10074.
3. Bergmeier SC, Katz SJ. 2002. A method for the parallel synthesis of multiply substituted oxazolidinones. J Comb Chem. 4: 162-166.
4. Bertau M, Bürli M, Hungerbühler E, Wagner P. 2001. A novel highly stereoselective synthesis of chiral 5- and 4,5-substituted 2-oxazolidinones. Tetrahedron: Asymmetry 12:2103 2107.
5. Bozdogan B, Appelbaum PC. 2004. Oxazolidinones: activity, mode of action, and mechanism of resistance. Int J Antimicrob. Agents 23:113-119.
6. Breeuwer P, Drocourt JL, Bunschoten N, Zwietering MH, Rombouts FM, Abee T. 1995. Characterizarion of uptake and hydrolysis of fluorescein diacetate and carboxyfluorescein diacetate by intracellular esterases in Saccharomyces cerevisiae, which result in accumulation of fluorescent product. Appl Environ Microbiol 61:1614-1619.
7. Cabon O, Buisson D, Larcheveque M, Azerad R. 1995. The microbial reduction of 2-chloro-3-oxoesters. Tetrahedron: Asymmetry 6:2199-2210.
8. Chin-Joe I, Nelisse PM, Straathof AJJ, Jongejan JA, Pronk JT, Heijnen JJ. 2000. Hydrolytic activity in baker's yeast limits the yield of asymmetric 3-oxo ester reduction. Biotechnol Bioeng 69:370-376.
9. Coelho F, Rossi RC. 2002. An approach to oxazolidin-2-ones from the Baylis-Hillman adducts. Formal synthesis of a chloramphenicol derivative. Tetrahedron Lett 43:2797-2800.
10. Datta J, Samanta TB. 1992. Characterization of a novel microsomal glutathione S-transferase produced by Aspergillus ochraceus TS. Mol. Cell. Biochem. 118:31-38.
11. De Kimpe, N, de Cock, W and Schamp, N (1987) A convenient synthesis of 1-chloro-2-alkanones. Synthesis 188-190.
12. Gordeev MF, Hackbarth C, Barbachyn MR, Banitt LS, Gage JR, Luehr GW, Gomez M, Trias J, Morin SE, Zurenko GE, Parker CN, Evans JM, White RJ, Patel DV. 2003. Novel oxazolidinone-quinolone hybrid antimicrobials. Bioorg Med Chem Lett 13:4213-4216.
13. Grogan G, Graf J, Jones A, Parsons S, Turner NJ, Flitsch SL. 2001. An asymmetric enzyme-catalyzed retro-Claisen reaction for the desymmetrization of cyclic β-diketones. Angew. Chem. 113:1145-1148. Angew Chem Int Ed 40:1111-1114.
14. Guilbault GG, Kramer DN. 1964. Fluorometric determination of lipase, acylase, α- and γ-chymotrypsin and inhibitors of these enzymes. Anal Chem 36:409-411.
15. Habig WH, Jakoby WB. 1981. Assays for differentiation of glutathione S-transferases. Methods Enzymol 77:398-405.
16. Iglesias E. 1997. Determination of keto-enol equilibrium constants and the kinetic study of the nitrosation reaction of β-dicarbonyl compounds. J Chem Soc Perkin Trans 2:431-439.
17. Jörg G, Bertau M. 2004. Fungal aerobic reductive dechlorination of ethyl 2-chloro-acetoacetate by Saccharomyces cerevisiae: mechanism of a novel type of microbial dehalogenation. ChemBioChem 5:87-92.
18. Jörg G, Leppchen K, Daußmann T, Bertau M. 2004. A novel convenient procedure for extractive work-up of whole-cell biotransformations using de-emulsifying hydrolases. Biotechnol Bioeng 87:525-536.
19. Naik S, Gopinath R, Goswami M, Patel BK. 2004. Chemoselective thioacetalisation and transthioacetalisation of carbonyl compounds catalysed by tetrabutylammonium tribromide (TBATB). Org Biomol Chem 2:1670-1677.
20. Nakamura K, Kawai Y, Ohno A. 1990. A novel method to synthesize (L)-(-hydroxyl esters by the reduction with bakers' yeast. Tetrahedron Lett 31:267-270.
21. Nishiyama T, Matsui S, Yamada F. 1986. Synthesis and spectral behavior of 5-methyl-3-phenyl-1,3-oxazolidin-2-ones using NMR. J Heterocycl Chem 23:1427-1429.
22. Ohta H, Kobayashi N, Sugai T. 1990. Reduction of acyl enolates of α-substituted β-keto esters by bakers' yeast. Agric Biol Chem 54:489-493.
23. Penninckx M. 2000. A short review on the role of glutathione in the response of yeasts to nutritional, environmental, and oxidative stresses. Enzyme Microb. Technol 26:737-742.
24. Phillips OA, Udo EE, Ali AAM, Al-Hassawi N. 2003. Synthesis and antibacterial activity of 5-substituted oxazolidinones. Bioorg Med Chem 11:35-41.
25. Rabasseda X, Sorbera LA, Castaner J. 1999. Befloxatone. Drugs Fut 24:1057-1067.
26. Schnürer J, Rosswall T. 1982. Fluorescein diacetate hydrolysis as a measure of total microbial activity in soil and litter. Appl Environ Microbiol 43:1256-1261.
27. Santaniello E, Manzocchi A. 2000. Biohydrogenation of unsaturated compounds mediated by fermenting baker's yeast. Trends Org Chem 8:21-34.
28. Sartori G, Ballini R, Bigi F, Bosica G, Maggi R, Righi P. 2004. Protection (and deprotection) of functional groups in organic synthesis by heterogeneous catalysis. Chem Rev 104:199-250.
29. Schäfer FQ, Büttner GR. 2001. Redox environment of the cell viewed through the redox state of the glutathione disulfide/glutathione couple. Free Radical Biol Med 30:1191-1212.
30. Thomasco LM, Gadwood RC, Weaver EA, Ochoada JM, Ford CW, Zurenko GE, Hamel JC, Stapert D, Moerman JK, Schaadt RD, Yagi BH. 2003. The synthesis and antibacterial activity of 1,3,4-Thiadiazole phenyl oxazolidinone analogues. Bioorg Med Chem Lett 13:4193-4196.
31. Tixidre, A, Zard, L, Rossey, G and Bourbon A. (1996), EP0736606.
32. Ushio K, Ebara K, Yamashita T. 1991. Selective inhibition of Renzymes by simple organic acids in yeast-catalysed reduction of ethyl 3-oxobutanoate. Enzyme Microb Technol 13:834-839.
33. Wakil SJ, Stoops JK, Joshi VC. 1983. Fatty acid synthesis and its regulation. Annu Rev Biochem 52:537-579.
34. Yagi BH, Zurenko GE. 1997. In vitro activity of linezolid and eperezolid, two novel oxazolidinone antimicrobial agents, against anaerobic bacteria. Anaerobe 3:301-306.
35. Yu C, Jiang Y, Liu B, Hu L. 2001. A facile synthesis of 2-oxazolidinones via Hofmann rearrangement mediated by bis(trifluoroacetoxy) iodobenzene. Tetrahedron Lett 42:1449-1452.
36. Zurenko GE, Gibson JK, Shinabarger DL, Aristoff PA, Ford CW, Tarpley WG. 2001. Oxazolidinones: a new class of antibacterials. Curr Opin Pharmacol 1:470-476.