Systematic assessment of the stability of benzaldehyde lyase in aqueous-organic biphasic systems and its stabilization by modification with methoxy-poly(ethylene) glycol

Journal of Molecular Catalysis B: Enzymatic

Volumn 67, Issue 3-4, 2010, Pages 208-213

  Van Den Wittenboer, Anne ^a   Niemeijer, Bernd ^a   Karmee, Sanjib Kumar ^a   Ansorge Schumacher, Marion B ^a,b  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Benzaldehyde lyase; mPEG modification; Organic solvent stability; Process stability

Indexed keywords

2-OCTANONE; BENZALDEHYDE LYASE; BIPHASIC SYSTEMS; C-C BONDS; COVALENT ATTACHMENT; IMMISCIBLE SOLVENTS; METHOXY; METHYL TERT BUTYL ETHER; MPEG MODIFICATION; ORGANIC BIPHASIC MEDIA; ORGANIC INTERFACES; ORGANIC PHASE; ORGANIC SOLVENT STABILITY; PROCESS STABILITY; PSEUDOMONAS FLUORESCENS; REACTION MEDIA; REACTIVE CONDITION; REVERSE REACTIONS; SOLUBLE SUBSTRATES; SOLVENT EFFECTS; STEREOSELECTIVE FORMATION; SYSTEMATIC ASSESSMENT; TECHNICAL APPLICATIONS;

ALDEHYDES; ENZYMES; ETHYLENE; GLYCOLS; KETONES; MOTION PICTURE EXPERTS GROUP STANDARDS; ORGANIC SOLVENTS; STABILIZATION; SUBSTRATES; SYSTEM STABILITY; TOLUENE; TOXICITY;

PHASE INTERFACES;

2 OCTANONE; ALDEHYDE; BENZALDEHYDE LYASE; ETHER DERIVATIVE; KETONE DERIVATIVE; LYASE; MACROGOL DERIVATIVE; METHYL TERT BUTYLETHER; TOLUENE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; ENZYME INACTIVATION; ENZYME MODIFICATION; ENZYME STABILITY; HALF LIFE TIME; SOLVENT EFFECT; SURFACE PROPERTY;

PSEUDOMONAS FLUORESCENS;

EID: 78049250758     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2010.08.007     Document Type: Article

References (47)

1. A.S. Demir, Ö. Sesenoglu, E. Eren, B. Hosrik, M. Pohl, E. Janzen, D. Kolter, R. Feldmann, P. Dünkelmann, and M. Müller Adv. Synth. Catal. 344 2002 96 103
2. A.S. Demir, Ö. Sesenoglu, P. Dünkelmann, and M. Müller Org. Lett. 5 2003 2047 2050
3. T. Hischer, D. Gocke, M. Fernández, P. Hoyos, A.R. Alcántara, J.V. Sinisterra, W. Hartmeier, and M.B. Ansorge-Schumacher Tetrahedron 61 2005 7378 7383
4. P. Domínguez de María, M. Pohl, D. Gocke, H. Gröger, H. Trauthwein, T. Stillger, L. Walter, and M. Müller Eur. J. Org. Chem. 2007 2940 2944
5. A.S. Demir, H. Hamamci, O. Sesenoglu, F. Aydogan, D. Capanoglu, and R. Neslihanoglu Tetrahedron Asymmetry 12 2001 1953 1956
6. U. Schörken, and G.A. Sprenger Biochim. Biophys. Acta 1385 1998 229 243
7. D. Enders, K. Breuer, and J.H. Teles Helv. Chim. Acta 79 1996 1217 1221
8. C.A. Dvorak, and V.H. Rawal Tetrahedron Lett. 39 1998 2925 2928
9. J. Pesch, K. Harms, and T. Bach Eur. J. Org. Chem. 2004 2025 2035
10. N. Nemeria, L. Korotchkina, M.J. McLeish, G.L. Kenyon, M.S. Patel, and F. Jordan Biochemistry 46 2007 10739 10744
11. P. Domínguez de María, T. Stillger, M. Pohl, S. Wallert, K. Drauz, H. Gröger, H. Trauthwein, and A. Liese J. Mol. Catal. B: Enzym. 38 2006 43 47
12. T. Stillger, Doctoral thesis, University of Bonn, 2004.
13. P. Fernandes, and J.M. Cabral G. Carrea, S. Riva, Organic Synthesis with Enzymes in Non-Aqueous Media 2008 VCH-Wiley Weinheim
14. M.H. Vermue, and J. Tramper Pure Appl. Chem. 67 1995 345 373
15. K. Martinek, A.N. Semenov, and I.V. Berezin Biochim. Biophys. Acta 658 1981 76 89
16. D.K. Eggers, H.W. Blanch, and J.M. Prausnitz Enzyme Microb. Technol. 11 1989 84 89
17. M.F. Eckstein, M. Peters, J. Lembrecht, A.C. Spiess, and L. Greiner Adv. Synth. Catal. 348 2006 1591 1596
18. D. Pollard, and B. Kosjek G. Carrea, S. Riva, Organic Synthesis with Enzymes in Non-Aqueous Media 2008 VCH-Wiley Weinheim
19. A.S. Ghatorae, M.J. Guerra, G. Bell, and P.J. Halling Biotechnol. Bioeng. 44 1994 1355 1361
20. A.C. Ross, G. Bell, and P.J. Halling J. Mol. Catal. B: Enzym. 8 2000 183 192
21. V.V. Mozhaev, Y.L. Khmelnitsky, M.V. Sergeeva, A.B. Belova, N.L. Klyachko, A.V. Levashov, and K. Martinek Eur. J. Biochem. 184 1989 597 602
22. Y.L. Khmelnitsky, A.B. Belova, A.V. Levashov, and V.V. Mozhaev FEBS Lett. 284 1991 267 269
23. T. Hischer, S. Steinsiek, and M.B. Ansorge-Schumacher Biocatal. Biotransform. 24 2006 437 442
24. M.B. Ansorge-Schumacher, L. Greiner, F. Schroeper, S. Mirtschin, and T. Hischer Biotechnol. J. 1 2006 564 568
25. M.B. Ansorge-Schumacher Mini Rev. Org. Chem. 4 2007 243 245
26. H. Iding, T. Dünnwald, L. Greiner, A. Liese, M. Müller, P. Siegert, P. Grötzinger, A.S. Demir, and M. Pohl Chem. Eur. J. 6 2000 1483 1495
27. A. van den Wittenboer, T. Schmidt, P. Müller, M.B. Ansorge-Schumacher, and L. Greiner Biotechnol. J. 4 2009 44 50
28. S.L. Snyder, and P.Z. Sobocinski Anal. Biochem. 64 1975 284 288
29. M.J. Hernáiz, J.M. Sánchez-Montero, and J.V. Sinisterra Biotechnol. Bioeng. 55 1997 252 260
30. U.K. Lämmli Nature 227 1970 680 685
31. D.R. Lide, CRC Handbook of Chemistry and Physics 89th ed. 2008 CRC Press, Taylor & Francis Group Boca Raton
32. A.A. Freitas, F.H. Quina, and F.A. Carroll J. Phys. Chem. B 101 1997 7488 7493
33. M.V. Filho, T. Stillger, M. Müller, A. Liese, and C. Wandrey Angew. Chem. Int. Ed. Engl. 42 2003 2993 2996
34. M. Biselli, U. Kragl, and C. Wandrey K. Drauz, H. Waldmann, Enzyme Catalysis in Organic Synthesis 2002 VCH-Wiley Weinheim
35. M. Di Lorenzo, A. Hidalgo, R. Molina, J.A. Hermoso, D. Pirozzi, and U.T. Bornscheuer Appl. Environ. Microbiol. 73 2007 7291 7299
36. H.K. Weber, J. Zuegg, K. Faber, and J. Pleiss J. Mol. Catal. B: Enzym. 3 1997 131 138
37. Y.L. Khmelnitsky, V.V. Mozhaev, A.B. Belova, M.V. Sergeeva, and K. Martinek Eur. J. Biochem. 198 1991 31 41
38. H. Ogino, and H. Ishikawa J. Biosci. Bioeng. 91 2001 109 116
39. G. DeSantis, and J.B. Jones Curr. Opin. Biotechnol. 10 1999 324 330
40. Q. Jene, J.C. Pearson, and C.R. Lowe Enzyme Microb. Technol. 20 1997 69 74
41. Y. Inada, K. Takahashi, T. Yoshimoto, A. Ajima, A. Matsushima, and Y. Saito Trends Biotechnol. 4 1986 190 194
42. J.A. Rodriguez-Martinez, R.J. Sola, B. Castillo, H.R. Cintron-Colon, I. Rivera-Rivera, G. Barletta, and K. Griebenow Biotechnol. Bioeng. 101 2008 1142 1149
43. B.N. Manjula, A. Tsai, R. Upadhya, K. Perumalsamy, P.K. Smith, A. Malavalli, K. Vandegriff, R.M. Winslow, M. Intaglietta, M. Prabhakaran, J.M. Friedman, and A.S. Acharya Bioconjug. Chem. 14 2003 464 472
44. D.I. Svergun, F. Ekstrom, K.D. Vandegriff, A. Malavalli, D.A. Baker, C. Nilsson, and R.M. Winslow Biophys. J. 94 2008 173 181
45. H. Garcia-Arellano, B. Valderrama, G. Saab-Rincon, and R. Vazquez-Duhalt Bioconjug. Chem. 13 2002 1336 1344
46. A.L. Soares, G.M. Guirmaraes, B. Polakiewicz, R.N.D. Pitombo, and J. Abrahao-Neto Int. J. Pharm. 237 2002 163 170
47. J.I. Lopez-Cruz, G. Viniegra-Gonzalez, and A. Hernandez-Arana Bioconjug. Chem. 17 2006 1093 1098