Trends and innovations in industrial biocatalysis for the production of fine chemicals

Current Opinion in Biotechnology

Volumn 15, Issue 4, 2004, Pages 272-279

  Panke, Sven ^a   Held, Martin ^a   Wubbolts, Marcel ^a  

^a DSM RESEARCH   (Netherlands)

Author keywords

deoxyribose 5 phosphate aldolase; DERA; ee; enantiomeric excess; lacto N tetraose; LNT; N acetyl d neuraminic acid; NeuAc; PDF; PEP; peptide deformylase; phosphoenolpyruvate

Indexed keywords

ALCOHOL; ALPHA AMINO ACID; AMIDE; AMINE; BETA AMINO ACID; CARBOHYDRATE; CARBOXYLIC ACID; EPOXIDE; NITRILE; PEPTIDE;

BIOCATALYST; BIOTECHNOLOGY; CHEMICAL INDUSTRY; ENANTIOMER; PRIORITY JOURNAL; REVIEW; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; AMINES; AMINO ACIDS; BIOTRANSFORMATION; CARBOHYDRATES; CATALYSIS; CHEMICAL INDUSTRY; ENZYMES; HYDROLASES; INDUSTRIAL MICROBIOLOGY; OXIDOREDUCTASES; PATENTS;

EID: 3543087310     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.copbio.2004.06.011     Document Type: Review

References (45)

1. M. Breuer, K. Ditrich, T. Habicher, B. Hauer, M. Kesseler, R. Stuermer and T. Zelinski Industrial methods for the production of optically active intermediates Angew Chem Int Ed Engl 43 2004 788 824 Excellent overview of current methods - both chemical and biocatalysis - applied in industry for the synthesis of enantiomerically pure compounds.
2. T. Li, A.B. Kootstra and I.G. Fotheringham Nonproteinogenic α-amino acid preparation using equilibrium shifted transamination Org Process Res Dev 6 2002 533 538 Elegant combination of an α- and δ-aminotransferase to produce l-α-amino acids in high yield.
3. O. May, S. Verseck, A. Bommarius and K. Drauz Development of dynamic kinetic resolution processes for biocatalytic production of natural and nonnatural l-amino acids Org Process Res Dev 6 2002 452 457
4. H. Trauthwein, O. May, U. Dingerdissen, S. Buchholz and K. Drauz A new biocatalytic route to enantiopure N-carbamoyl amino acids by fast enzyme screening Tetrahedron Lett 44 2003 3737 3739
5. T.H.P. Maier Semisynthetic production of unnatural l-α-amino acids by metabolic engineering of the cysteine-biosynthetic pathway Nat Biotechnol 21 2003 422 427 Breakthrough methodology for the manufacture of a variety of unnatural (S)-α-amino acids by fermentation/biotransformation based on the cysteine biosynthesis pathway.
6. T. Sonke, B. Kaptein, A.F.V. Wagner, P.J.L.M. Quaedflieg, S. Schultz, S. Ernste, A. Schepers, J.H.M. Mommers and Q.B. Broxterman Peptide deformylase as biocatalyst for the synthesis of enantiomerically pure amino acid derivatives J Mol Catal, B Enzym 29 2004 265 277
7. M. Preiml, K. Hillmayer and N. Klempier A new approach to β-amino acids: biotransformation of N-protected β-amino nitriles Tetrahedron Lett 44 2003 5057 5059
8. F. Balkenhohl, K. Ditrich, B. Hauer and W. Ladner Optically active amines via lipase-catalyzed methoxyacetylation Chemiker-Zeitung 339 1997 381 384
9. Matuschek M, Stuermer R, Hauer B, Klebe G, Bocola M: Lipase variants, their production with recombinant cells, and their use in alcohol or amine acylation and ester hydrolysis. 2002, Patent EP11620[2003035878].
10. Greenberg W, Weiner DP, Adger B, Burk M: High throughput screening of nitroreductases and use of the enzyme for biocatalytic reduction of nitro compounds and production of amines. 2003, Patent US2177[2003062399].
11. R. Broxterman and H. Kierkels Synthesis of enantiopure functionalised amines using biocatalysis Speciality Chemicals Magazine 22 2002 9 11
12. R. Öhrlein and G. Baisch Chemo-enzymatic approach to statin side-chain building blocks Adv Synthesis Catalysis 345 2003 713 715
13. M. Wolberg, W. Hummel, C. Wandrey and M. Müller Highly regio- and enantioselective reduction of 3,5-dioxocarboxylates Angew Chem Int Ed Engl 39 2000 4306 4308
14. W.A. Greenberg, A. Varvak, S.R. Hanson, K. Wong, H.J. Huang, P. Chen and M.J. Burk Development of an efficient, scalable, aldolase-catalyzed process for enantioselective synthesis of statin intermediates Proc Natl Acad Sci USA 101 2004 5788 5793 Good illustration of the potential of DERA and aldolases in general for industrial asymmetric synthesis.
15. Kierkels JGT, Mink D, Panke S, Lommen FAM, Heemskerk D: Process for the preparation of 2,4-dideoxyhexoses and 2,4,6-trideoxyhexoses. 2003, Patent WO 03/006656 A2.
16. C.H. Wong, E. Garciajunceda, L.R. Chen, O. Blanco, H.J.M. Gijsen and D.H. Steensma Recombinant 2-deoxyribose-5-phosphate aldolase in organic synthesis - use of sequential 2-substrate and 3-substrate aldol reactions J Am Chem Soc 117 1995 3333 3339
17. G. Desantis, J.J. Liu, D.P. Clark, A. Heine, I.A. Wilson and C.H. Wong Structure-based mutagenesis approaches toward expanding the substrate specificity of d-2-deoxyribose-5-phosphate aldolase Bioorg Med Chem 11 2003 43 52
18. P.L. Brower, D.E. Butler, C.F. Deering, T.V. Le, A. Millar, T.N. Nanninga and B.D. Roth The synthesis of (4R-cis)-1,1-dimethylethyl 6-cyanomethyl-2,2- dimethyl-1,3-dioxane-4-acetate, a key intermediate for the preparation of CI-981, a highly potent, tissue selective inhibitor of HMG-CoA reductase Tetrahedron Lett 33 1992 2279 2282
19. Burk M, Desantis G, Morgan B, Zhu Z: Manufacture of (R)-ethyl 4-cyano-3-hydroxybutyric acid from 3-hydroxyglutaronitrile using nitrilases. 2002, Patent WO2003106415A2.
20. K. Abokitse and W. Hummel Cloning, sequence analysis, and heterologous expression of the gene encoding a (S)-specific alcohol dehydrogenase from Rhodococcus erythropolis DSM 43297 Appl Microbiol Biotechnol 62 2003 380 386
21. W. Hummel, K. Abokitse, K. Drauz, C. Rollmann and H. Groger Towards a large-scale asymmetric reduction process with isolated enzymes: expression of an (S)-alcohol dehydrogenase in E. coli and studies on the synthetic potential of this biocatalyst Adv Synthesis Catalysis 345 2003 153 159
22. H. Slusarczyk, S. Felber, M.R. Kula and M. Pohl Stabilization of NAD-dependent formate dehydrogenase from Candida boidinii by site-directed mutagenesis of cysteine residues Eur J Biochem 267 2000 1280 1289
23. H. Gröger, W. Hummel, C. Rollmann, F. Chamouleau, H. Husken, H. Werner, H. Gröger, C. Wunderlich, K. Abokitse, K. Drauz and S. Buchholz Preparative asymmetric reduction of ketones in a biphasic medium with an (S)-alcohol dehydrogenase under in situ cofactor-recycling with a formate dehydrogenase Tetrahedron 60 2004 633 640 Reports the use of a two-liquid phase process for enantioselecive ketone reduction to reduce substrate mass-transfer limitations.
24. W. Stampfer, B. Kosjek, C. Moitzi, W. Kroutil and K. Faber Biocatalytic asymmetric hydrogen transfer Angew Chem Int Ed Engl 41 2002 1014 1017 An elegant system for manufacturing (S)-alcohols. One enzyme is responsible for both reduction and cofactor regeneration. The hydrogen donor can be added in large quantitites to the aqueous phase, driving the reaction to completion and modifying the polarity of the medium at the same time.
25. W. Stampfer, B. Kosjek, K. Faber and W. Kroutil Biocatalytic asymmetric hydrogen transfer employing Rhodococcus ruber DSM 44541 J Org Chem 68 2003 402 406
26. B. Kosjek, W. Stampfer, M. Pogorevc, W. Goessler, K. Faber and W. Kroutil Purification and characterization of a chemotolerant alcohol dehydrogenase applicable to coupled redox reactions Biotechnol Bioeng 86 2004 55 62
27. W. Stampfer, K. Edegger, B. Kosjek, K. Faber and W. Kroutil Simple biocatalytic access to enantiopure (S)-1-heteroarylethanols employing a microbial hydrogen transfer reaction Adv Synthesis Catalysis 346 2004 57 62
28. M. Mahmoudian, D. Noble, C.S. Drake, R.F. Middleton, D.S. Montgomery, J.E. Piercey, D. Ramlakhan, M. Todd and M.J. Dawson An efficient process for the production of N-acetylneuraminic acid using N-acetylneuraminic aldolase Enzyme Microb Technol 20 1997 393 400
29. Wong C-H: Method for synthesizing 2-ketoaldonic acids. 1998, Patent US 5.759.825.
30. B. Zelic, T. Gerharz, M.C. Bott, D. Vasic-Racki, C. Wandrey and R. Takors Fed-batch process for pyruvate production by recombinant Escherichia coli YYC202 strain Eng Life Sci 3 2003 299 305
31. U. Kragl, D. Gygax, O. Ghisalba and C. Wandrey Enzymatic two-step synthesis of N-acetylneuraminic acid in the enzyme membrane reactor Angew Chem Int Ed Engl 30 1991 827 828
32. K. Tabata, S. Koizumi, T. Endo and A. Ozaki Production of N-acetyl-d-neuraminic acid by coupling bacteria expressing N-acetyl-d- glucosamine 2-epimerase and N-acetyl-d-neuraminic acid synthetase Enzyme Microb Technol 30 2002 327 333
33. K.M. Koeller and C.H. Wong Emerging themes in medicinal glycoscience Nat Biotechnol 18 2000 835 841
34. R. Ramphal, C. Carnoy, S. Fievre, J.C. Michalski, N. Houdret, G. Lamblin, G. Strecker and P. Roussel Pseudomonas aeruginosa recognizes carbohydrate chains containing type 1 (Galβ1-3GlcNAc) or type 2 (Galβ1-4GlcNAc) disaccharide units Infect Immun 59 1991 700 704
35. M. Watanabe, K. Miyake, K. Yanae, Y. Kataoka, S. Koizumi, T. Endo, A. Ozaki and S. Iijima Molecular characterization of a novel β1,3- galactosyltransferase for capsular polysaccharide synthesis by Streptococcus agalactiae type Ib J Biochem (Tokyo) 131 2002 183 191
36. Endo T, Koizumi S: Preparation of β-1,3-N-acetylglucosamine transferase from Pasteurella multocida and the use of the enzyme for N-acetylglucosamine-containing polysaccharide synthesis. 2003, Patent WO2003035877A1.
37. S. Koizumi, T. Endo, K. Tabata and A. Ozaki Large-scale production of UDP-galactose and globotriose by coupling metabolically engineered bacteria Nat Biotechnol 16 1998 847 850
38. K. Tabata, S. Koizumi, T. Endo and A. Ozaki Production of UDP-N-acetylglucosamine by coupling metabolically engineered bacteria Biotechnol Lett 22 2000 479 483
39. S. Jennewein and R. Croteau Taxol: biosynthesis, molecular genetics, and biotechnological applications Appl Microbiol Biotechnol 57 2001 13 19
40. R.N. Patel Tour de paclitaxel: biocatalysis for semisynthesis Annu Rev Microbiol 52 1998 361 395
41. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth and H. Reichenbach Antibiotics from gliding bacteria. 77. Epothilone A and B - novel 16-membered macrolides with cytotoxic activity: isolation, crystal structure, and conformation in solution Angew Chem Int Ed Engl 35 1996 1567 1569
42. D.C. Myles Novel biologically active natural and unnatural products Curr Opin Biotechnol 14 2003 627 633
43. Favreau D, Levesque K, Guo Z, James BL, Wang S, Kant J: Method of preparation of 21-amino epothilone derivatives. 2003, Patent WO03070170.
44. Ashley GW, Metcalf B, Tang L, Katz L, Lau J, Licari P: Novel epothilone compounds and methods for making the same. 2003, Patent WO03042217.
45. A. Glieder, R. Weis, W. Skranc, P. Pöchlauer, I. Dreveny, S. Majer, M. Wubbolts, H. Schwab and K. Gruber Comprehensive step-by-step engineering of an (R)-hydroxynitrile lyase for large-scale asymmetric synthesis Angew Chem Int Ed Engl 42 2003 4815 4818 Successful development of an industrial biotransformation process, covering the steps from gene cloning and expression through rational improvement of activity to application.