The production of fine chemicals by biotransformations

Current Opinion in Biotechnology

Volumn 13, Issue 6, 2002, Pages 548-556

  Straathof, Adrie J J ^a   Panke, Sven ^b   Schmid, Andreas ^b  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

^b ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 QUINOXALINECARBOXYLIC ACID; BETA LACTAM DERIVATIVE; CHEMICAL AGENT; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; HYDROLASE; HYDROXYMETHYLGLUTARYL COENZYME A REDUCTASE INHIBITOR; LAMIVUDINE; LOBUCAVIR; LONAFARNIB; LOTRAFIBAN; OMAPATRILAT; PACLITAXEL; POSACONAZOLE; RENIN INHIBITOR; RUPINTRIVIR; TALAMPANEL; XEMILOFIBAN; DRUG; ENZYME;

BIOCATALYST; BIOTRANSFORMATION; CATALYSIS; CHEMICAL INDUSTRY; CHIRALITY; CONCENTRATION (PARAMETERS); DRUG INDUSTRY; NONHUMAN; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REVIEW; SYNTHESIS; BIOTECHNOLOGY; METABOLISM; METHODOLOGY; MICROBIOLOGY; QUALITY CONTROL;

BIOTECHNOLOGY; BIOTRANSFORMATION; CATALYSIS; CHEMICAL INDUSTRY; DRUG INDUSTRY; ENZYMES; INDUSTRIAL MICROBIOLOGY; PHARMACEUTICAL PREPARATIONS; QUALITY CONTROL;

EID: 0036900263     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(02)00360-9     Document Type: Review

References (48)

1. Cheetham P.S.J. Case studies in the application of biocatalysts for the production of (bio)chemicals. Straathof A.J.J., Adlercreutz P. Applied Biocatalysis. edn 2:2000;93-152 Harwood Scientific Publishers, Amsterdam. This is a chapter in a useful textbook that covers all aspects of applied biocatalysis. The chapter describes about 20 industrial biotransformations in detail and lists many more.
2. Liese A., Seelbach K., Wandrey C. Industrial Biotransformations. 2000;Wiley-VCH, Weinheim, Germany. The authors of this book did a wonderful job of collecting quantitative data about most industrial processes that involve a single or two enzymatic reactions.
3. Flickinger M.C., Drew S.J. Encyclopedia of Bioprocess Technology. 1999;Marcel Dekker, New York.
4. Schmid A., Dordick J.S., Hauer B., Kiener A., Wubbolts M., Witholt B. Industrial biocatalysis today and tomorrow. Nature. 409:2001;258-268.
5. Ogawa J., Shimizu S. Microbial enzymes: new industrial applications from traditional screening methods. Trends Biotechnol. 17:1999;13-21.
6. Schulze B., Wubbolts M.G. Biocatalysis for industrial production of fine chemicals. Curr Opin Biotechnol. 10:1999;609-615.
7. Rasor J.P., Voss E. Enzyme-catalyzed processes in pharmaceutical industry. Appl Catal A: Gen. 221:2001;145-158.
8. Zaks A. Industrial biocatalysis. Curr Opin Chem Biol. 5:2001;130-136.
9. Ghisalba O. Biocatalyzed reactions. Gualtieri F. New Trends in Synthetic Medicinal Chemistry. 2000;189-219 Wiley-VCH, Weinheim, Germany.
10. Hashimoto S., Ozaki A. Whole microbial cell processes for manufacturing amino acids, vitamins or ribonucleotides. Curr Opin Biotechnol. 10:1999;604-608.
11. Bruggink A. Synthesis of β-Lactam Antibiotics. 2001;Kluwer, Dordrecht, The Netherlands.
12. Patel R.N. Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances. Curr Opin Biotechnol. 12:2001;587-604.
13. Manzoni M., Rollini N. Biosynthesis and biotechnological production of statins by filamentous fungi and application of these cholesterol-lowering drugs. Appl Microbiol Biotechnol. 58:2002;555-564.
14. Faber K. Biotransformations in Organic Chemistry. edn 4:2000;Springer-Verlag, Berlin, Germany. A standard introductory textbook on the use of enzymes as catalysts in organic synthesis, describing the main principles and concepts. Selected application examples are supported by numerous references to the original literature.
15. Chin-Joe I., Straathof A.J.J., Pronk J.T., Jongejan J.A., Heijnen J.J. Influence of the ethanol and glucose supply rate on the rate and enantioselectivity of 3-oxo ester reduction by baker's yeast. Biotechnol Bioeng. 75:2001;29-38.
16. Freeman A., Lilly M.D. Effect of processing parameters on the feasibility and operational stability of immobilized viable microbial cells. Enzyme Microb Technol. 23:1998;335-345.
17. Wöltinger J., Drauz K.H., Bommarius A.S. The membrane reactor in the fine chemicals industry. Appl Catal A: Gen. 221:2001;171-185.
18. Thomas S.M., DiCosimo R., Nagarajan V. Biocatalysis: applications and potentials for the chemical industry. Trends Biotechnol. 20:2002;238-242.
19. van de Sandt E.J.A.X., De Vroom E. Innovations in cephalosporin and penicillin production: painting the antibiotics industry green. Chimica Oggi. 18:2000;72-75. Overview of DSM's successful efforts in introducing biotransformation or metabolic engineering to replace chemical processes.
20. Hieber G., Ditrich K. Introducing ChiPros™ - biocatalytic production of chiral intermediates on a commercial scale. Chimia Oggi. 19:2001;16-20.
21. Wegman M.A., Hacking M.A.P.J., Rops J., Pereira P., Van Rantwijk F., Sheldon R.A. Dynamic kinetic resolution of phenylglycine esters via lipase-catalysed ammonolysis. Tetrahedron Asymmetry. 10:1999;1739-1750.
22. Lye G.J., Woodley J.M. Application of in situ product-removal techniques to biocatalytic processes. Trends Biotechnol. 17:1999;395-402.
23. Panke S., Held M., Wubbolts M.G., Witholt B., Schmid A. Pilot scale production of (S) styrene oxide from sytrene by recombinant Escherichia coli synthesizing styrene monooxygenase. Biotechnol Bioeng. 80:2002;33-41.
24. Matsumae H., Akatsuka H., Shibatani T. Diltiazem synthesis. Flickinger M.C., Drew S.J. Encyclopedia of Bioprocess Technology. 2:1999;823-840 Marcel Dekker, Inc, New York.
25. Mahmoudian M., Dawson M.J. Chemoenzymatic production of the antiviral agent Epivir. Strohl W.R. Biotechnology of Antibiotics. edn 2:1997;753-775 Marcel Dekker, Inc, New York.
26. Blaser H.U., Spindler F., Studer M. Enantioselective catalysis in fine chemicals production. Appl Catal A: Gen. 221:2001;119-143. A detailed discussion about the use of chemical catalysts for the production of chiral compounds. The numerous examples given describe processes on production and pilot scale in various companies.
27. Sonke T., Kaptein B., Boesten W.H.J., Broxterman Q.B., Schoemaker H.E., Kamphuis J., Formaggio F., Toniolo C., Rutjes F.P.J.T. Aminoamidase-catalyzed preparation and further transformations of enantiopure α-hydrogen- and α,α-disubstituted α-amino acids. Patel R.N. Stereoselective Biocatalysis. 2000;23-58 Marcel Dekker, Inc, New York.
28. Bommarius A.S., Drauz K., Klenk H., Wandrey C. Operational stability of enzymes - acylase-catalyzed resolution of N-acetyl amino-acids to enantiomerically pure L-amino acids. Ann NY Acad Sci. 672:1992;126-136.
29. Bommarius A.S., Schwarm M., Drauz K. Biocatalysis to amino acid-based chiral pharmaceuticals - examples and perspectives. J Mol Catal B: Enzym. 5:1998;1-11.
30. Ellis L.B.M., Hershberger C.D., Bryan E.M., Wackett L.P. The University of Minnesota biocatalysis/biodegradation database: emphasizing enzymes. Nucleic Acids Res. 29:2001;340-343. An introduction to the Biocatalysis/Biodegradation database. The database is very well maintained and contains detailed information about enzymes, reactions, and the corresponding metabolic pathways. Entries are linked to other databases.
31. Cowan D.A. Microbial genomes - the untapped resource. Trends Biotechnol. 18:2000;14-16.
32. Saksena A.K., Girijavallabhan V.M., Lovey R.G., Pike R.E., Wang H.Y., Ganguly A.K., Morgan B., Zaks A., Puar M.S. Highly stereoselective access to novel 2,2,4-trisubstituted tetrahydrofurans by halocyclization - practical chemoenzymatic synthesis of Sch-51048, a broad-spectrum orally-active antifungal agent. Tetrahedron Lett. 36:1995;1787-1790.
33. Stead P., Marley H., Mahmoudian M., Webb G., Noble D., Ip Y.T., Piga E., Rossi T., Roberts S.M., Dawson M.J. Efficient procedures for the large-scale preparation of (1S,2S)-trans-2-methoxycyclohexanol, a key chiral intermediate in the synthesis of tricyclic β-lactam antibiotics. Tetrahedron Asymmetry. 7:1996;2247-2250.
34. Walsgrove T.C., Powell L., Wells A. A practical and robust process to produce SB-214857, Lotrafiban, ((2S)-7-(4,4′-bipiperidinylcarbonyl)-2,3,4,5-tetrahydro-4-methyl-3- oxo-1H-1,4-benzodiazepine-2-acetic acid) utilising an enzymic resolution as the final step. Org Proc Res Develop. 2:2002;488-491.
35. Patel R.N., Banerjee A., Ko R.Y., Howell J.M., Li W.-S., Comezoglu F.T., Partyka R.A., Szarka L. Enzymic preparation of (3R-cis)-3-(acetyloxy)-4-phenyl-2-azetidinone: a taxol side-chain synthon. Biotechnol Appl Biochem. 20:1994;23-33.
36. Patel R.N., McNamee C.M., Szarka L.J. Enantioselective enzymatic acetylation of racemic 4-4-α,6-β(E)-6-4,4-bis(4-fluorophenyl)-3-(1-methyl-1H-tetrazol-5- yl)-1,3-butadienyl-tetrahydro-4-hydroxy-2H-pyran-2-one. Appl Microbiol Biotechnol. 38:1992;56-60.
37. Morgan B., Zaks A., Dodds D.R., Liu J.C., Jain R., Megati S., Njoroge F.G., Girijavallabhan V.M. Enzymatic kinetic resolution of piperidine atropisomers: synthesis of a key intermediate of the farnesyl protein transferase inhibitor, SCH66336. J Org Chem. 65:2000;5451-5459.
38. Landis B.H., Mullins P.B., Mullins K.E., Wang P.T. Kinetic resolution of β-amino esters by acylation using immobilized penicillin amidohydrolase. Org Proc Res Dev. 6:2002;539-546.
39. Doswald S., Estermann H., Kupfer E., Stadler H., Walther W., Wesisbrod T., Wirz B., Wostl W. Large scale preparation of chiral building blocks for the P3 site of renin inhibitors. Bioorg Med Chem. 2:1994;403-410.
40. Mahmoudian M., Baines B.S., Drake C.S., Hale R.S., Jones P., Piercey J.E., Montgomery D.S., Purvis I.J., Storer R., Dawson M.J., et al. Enzymatic production of optically pure (2′R-cis)-2′deoxy-3′tiacytidine (3TC, Lamivudine): a potent anti HIV agent. Enzyme Microb Technol. 15:1993;749-755.
41. Tao J., McGee K. Development of a continuous enzymatic process for the preparation of (R)-3-(4-fluorophenyl)-2-hydroxy propionic acid. Org Proc Res Develop. 6:2002;520-524.
42. Schmidt E., Ghisalba O., Gygax D., Sedelmeier G. Optimization of a process for the production of (R)-2-hydroxy-phenylbutyric acid - an intermediate for inhibitors of angiotensin-converting enzyme. J Biotechnol. 24:1992;315-327.
43. Vicenzi J.T., Zmijewski M.J., Reinhard M.R., Landen B.E., Muth W.L., Marler P.G. Large-scale stereoselective enzymatic ketone reduction with in situ product removal via polymeric adsorbent resins. Enzyme Microb Technol. 20:1997;494-499.
44. Patel R.N. Enzymatic synthesis of chiral intermediates for Omapatrilat, an antihypertensive drug. Biomol Eng. 17:2001;167-182. Excellent example of the multiple facets of biotransformation development for a drug, albeit on rather a small scale, at Bristol-Myers Squibb.
45. Landis B.H., Laughlin J.K., Heeren R., Grabner R.W., Wang P.T. Bioconversion of N-butylglucamine to 6-deoxy-6-butylamino sorbose by Gluconobacter oxydans. Org Proc Res Dev. 6:2002;547-552.
46. Wong J.W., Watson Jr H.A., Bouressa J.F.B., Cawley J.C., Doro A.E., Guzek D.B., Hintz M.A., McCormick E.L., Scully D.A., Siderewicz J.M., et al. Biocatalytic oxidation of 2-methylquinoxaline to 2-quinoxalinecarboxylic acid. Org Proc Res Dev. 6:2002;477-481.
47. Gbewonyo K., Buckland B.C., Lilly M.D. Development of a large-scale continuous substrate feed process for the biotransformation of Simvastatin by Nocardia sp. Biotechnol Bioeng. 37:1991;1101-1107.
48. Hanson R.L., Shi Z.P., Brzozowski D.B., Banerjee A., Kissick T.P., Singh J., Pullockaran A.J., North J.T., Fan J.Y., Howell J., et al. Regioselective enzymatic aminoacylation of lobucavir to give an intermediate for lobucavir prodrug. Bioorg Med Chem. 8:2000;2681-2687.