Stability, activity, and selectivity of benzaldehyde lyase in supercritical fluids

Journal of Supercritical Fluids

Volumn 62, Issue , 2012, Pages 173-177

  Natalia, Dessy ^a   Greiner, Lasse ^a,b   Leitner, Walter ^a   Ansorge Schumacher, Marion B ^c  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b KARL WINNACKER INSTITUT   (Germany)

^c TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Hydroxy ketones; Benzaldehyde lyase; Biotransformation; Enzyme catalysis; Furaldehyde; Supercritical fluids

Indexed keywords

BENZALDEHYDE LYASE; BIOTRANSFORMATION; ENZYME CATALYSIS; FURALDEHYDE; SUPER-CRITICAL;

ALDEHYDES; CARBON DIOXIDE; CATALYST SELECTIVITY; EFFLUENT TREATMENT; ENANTIOSELECTIVITY; ETHANE; KETONES; ORGANIC COMPOUNDS; STABILITY; SULFUR; SULFUR DIOXIDE; SULFUR HEXAFLUORIDE; SUPERCRITICAL FLUID EXTRACTION; SUPERCRITICAL FLUIDS; SYNTHESIS (CHEMICAL);

ENZYME ACTIVITY;

EID: 84855854223     PISSN: 08968446     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.supflu.2011.11.025     Document Type: Article

References (38)

1. i-requiring enzyme, from Pseudomonas fluorescens Biovar I J. Bacteriology 171 1989 2401 2405
2. T.G. Mosbacher, M. Müller, and G.E. Schulz Structure and mechanism of the ThDP-dependent benzaldehyde lyase from Pseudomonas fluorescens FEBS J. 272 2005 6067 6076 (Pubitemid 41713696)
3. A. Maraite, T. Schmidt, M.B. Ansorge-Schumacher, M. Brzozowski, and G. Grogan Structure of ThDP-dependent benzaldehyde lyase refined to 1.65 resolution Acta Cristallographica 63 2007 546 548 (Pubitemid 47052196)
4. A.S. Demir, M. Pohl, E. Janzen, and M. Müller Enantioselective synthesis of hydroxy ketones through cleavage and formation of acyloin linkage. Enzymatic kinetic resolution via CC bond cleavage J. Chemical Society, Perkin Transactions 1 2001 633 635
5. E. Janzen, M. Müller, D. Kolter-Jung, M.M. Kneen, M.J. McLeish, and M. Pohl Characterization of benzaldehyde lyase from Pseudomonas fluorescens: a versatile enzyme for asymmetric CC bond formation Bioorganic Chemistry 34 2006 345 361 (Pubitemid 44709162)
6. M.B. Ansorge-Schumacher, L. Greiner, F. Schroeper, S. Mirtschin, and T. Hischer Operational concept for the improved synthesis of (R)-3,3′-furoin and related hydrophobic compounds with benzaldehyde lyase Biotechnology J. 1 2006 564 568
7. T. Hischer, D. Gocke, M. Fernández, P. Hoyos, A.R. Alcantara, J.V. Sinisterra, W. Hartmeier, and M.B. Ansorge-Schumacher Stereoselective synthesis of novel benzoins catalysed by benzaldehyde lyase in a gel-stabilised two-phase system Tetrahedron 61 2005 7378 7383 (Pubitemid 40941602)
8. A.S. Demir, O. Sesenoglu, P. Dünkelmann, and M. Müller Benzaldehyde lyase-catalyzed enantioselective carboligation of aromatic aldehydes with mono- and dimethoxy acetaldehyde Organic Letters 5 2003 2047 2050 (Pubitemid 37140923)
9. R.J. Mikolajek, A.C. Spiess, M. Pohl, S. Lamare, and J. Buchs An activity, stability and selectivity comparison of propioin synthesis by thiamine diphosphate-dependent enzymes in a solid/gas bioreactor Chembiochem: A European Journal of Chemical Biology 8 2007 1063 1070 (Pubitemid 47183623)
10. M. Pohl, B. Lingen, and M. Müller Thiamine-diphosphate-dependent enzymes: new aspects of asymmetric CC bond formation Chemistry: A European J. 8 2002 5288 5295 (Pubitemid 35453332)
11. P. Dominguez de María, T. Stillger, M. Pohl, S. Wallert, K. Drauz, H. Groger, H. Trauthwein, and A. Liese Preparative enantioselective synthesis of benzoins and (R)-2-hydroxy-1-phenylpropanone using benzaldehyde lyase J. Molecular Catalysis B: Enzymatic 38 2006 43 47 (Pubitemid 43028553)
12. P. Dominguez de María, M. Pohl, D. Gocke, H. Groger, H. Trauthwein, T. Stillger, L. Walter, and M. Müller Asymmetric synthesis of aliphatic 2-hydroxy ketones by enzymatic carboligation of aldehydes European J. Organic Chemistry 18 2007 2940 2944
13. S. Shanmugananthan, D. Natalia, A. van den Wittenboer, C. Kohlmann, L. Greiner, and P. Dominguez de Maria Enzyme-catalyzed CC bond formation using 2-methyltetrahydrofuran (2-MTHF) as (co)solvent: efficient and bio-based alternative to DMSO and MTBE Green Chemistry 12 2010 2240 2245
14. M. Peters, M.F. Eckstein, G. Hartjen, A.C. Spiess, W. Leitner, and L. Greiner Exploring conversion of biphasic catalytic reactions: analytical solution and parameter study Industrial & Engineering Chemistry Research 46 2007 7073 7078 (Pubitemid 350069756)
15. A. van den Wittenboer, T.W. Schmidt, P. Müller, M.B. Ansorge-Schumacher, and L. Greiner Biphasic mini-reactor for characterization of biocatalyst performance Biotechnology J. 4 2009 44 50
16. A. van den Wittenboer, B. Niemeijer, S.K. Karmee, and M.B. Ansorge-Schumacher Systematic assessment of the stability of benzaldehyde lyase in aqueous-organic biphasic systems and its stabilisation by modification with methoxy-poly(ethylene)glycol J. Molecular Catalysis B: Enzymatic 67 2010 208 213
17. N. Bieler, M.B. Ansorge.Schumacher, and L. Greiner Automated lab-scale production of PVA/PEG-enzyme immobilisates Biotechnology J. 5 2010 881 885
18. M.B. Ansorge-Schumacher Biocatalyzed asymmetric syntheses using gel-stabilized aqueous organic two-phase system D. Enders, K.E. Jaeger, Asymmetric Synthesis with Chemical and Biological Methods 2007 Wiley-VCH Verlag GmBH & Co. KGaA Weinheim, Germany 427 434
19. A.J. Mesiano, E.J. Beckman, and A.J. Russell Supercritical biocatalysis Chemical Reviews 99 1999 623 634
20. D.C. Steytler, P.S. Moulson, and J. Reynolds Biotransformations in near-critical carbon dioxide Enzyme and Microbial Technology 13 1991 221 226
21. Z. Knez Enzymatic reactions in dense gases The J. Supercritical Fluids 47 2009 357 372
22. D.A. Hammond, M. Karel, and A.M. Klibanov Enzymatic reactions in supercritical gases Applied Biochemistry and Biotechnology 11 1985 393 400
23. 2-based supercritical fluids Biotechnology J. 3 2008 104 111 (Pubitemid 351200937)
24. C. Roosen, P. Müller, and L. Greiner Ionic liquids in biotechnology: applications and perspectives for biotransformations Applied Microbial Biotechnology 81 2008 607 614
25. M. Pohl, M. Müller, A. Demir, Nucleotide sequence encoding a benzaldehyde lyase, and process for stereoselectively synthesizing 2-hydroxyketones, US Patent 7,045,334 B2, May 16, 2006.
26. D. Natalia, C. Kohlmann, M.B. Ansorge-Schumacher, and L. Greiner Direct spectrophotometric assay for benzaldehyde lyase activity Biotechnology Research International 2011 2011 Article ID 478925
27. S. Lamare, M.-D. Legoy, and M. Graber Solid/gas bioreactors: powerful tools for fundamental research and efficient technology for industrial applications Green Chemistry 6 2004 445 458 (Pubitemid 39472342)
28. W. Tedjo, M.N. Eshtiaghi, and D. Knorr Impact of supercritical carbon dioxide and high pressure on lypoxygenase and peroxidase activity J. Food Science 65 2000 1284 1287 (Pubitemid 32102932)
29. C. Roosen, M.B. Ansorge-Schumacher, T. Mang, W. Leitner, and L. Greiner Gaining pH-control in water/carbon dioxide biphasic systems Green Chemistry 9 2007 455 458
30. T.J. Ahern, and A.M. Klibanov The mechanism of irreversible enzyme inactivation at 100 °C Science 228 1985 1280 1283
31. S. Kamat, J. Barrera, and E.J. Beckman Biocatalytic synthesis of acrylates in organic solvents and supercritical fluids: 1. Optimization of enzyme environment Biotechnology and Bioengineering 40 1992 158 166
32. S. Kamat, B. Iwaskewycz, E.J. Beckman, and A.J. Russell Biocatalytic synthesis of acrylates in organic solvents and supercritical fluids: tuning enzyme activity by changing pressure Proceeding of the National Academy of Sciences of the USA 90 1993 2940 2944 (Pubitemid 23113533)
33. National Institute of Standard and Technology (NIST), Standard Reference Data Program, United State of America, November 6. Available from: http://webbook.nist.gov, 2008.
34. M.B. Ansorge-Schumacher Immobilisation of biological catalysts Ertl Krötzinger Schüth Weitkamp Handbook of Heterogeneous Catalysis 2008 Wiley VCH Weinheim 978-3-527-31241-2 vol. 1, pp. 644-655
35. C. Mateo, J.M. Palomo, G. Fernández-Lorente, J.M. Guisan, and R. Fernández-Lafuente Improvemenent of enzyme activity, stability and selectivity via immobilization techniques Process Biochemistry 40 2007 1451 1463 (Pubitemid 46482654)
36. P.V. Iyer, L. Ananthanarayan, Enzyme stabilization - aqueous and non-aqueous environment, 43 (2008) 1019-1032.
37. R. Fernández-Lafuente Stabilization of multimeric enzymes: strategies to prevent subunit dissociation Enzyme and Microbial Technology 45 2009 405 418
38. K. Hernández, and R. Fernández-Lafuente Control of protein immobilisation: coupling immobilisation and site-directed mutagenesis to improve biocatalyst or biosensor performance Enzyme and Microbial Technology 48 2011 107 122