Production of fine chemicals using biocatalysis

Current Opinion in Biotechnology

Volumn 10, Issue 6, 1999, Pages 595-603

  Liese, Andreas ^a   Villela Filho, Murillo ^a  

^a FORSCHUNGSZENTRUM JÜLICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL AGENT;

BIOTECHNOLOGY; BIOTRANSFORMATION; CATALYST; CHEMICAL REACTION; CHEMISTRY; DEGRADATION; INDUSTRY; MOLECULAR STABILITY; NONHUMAN; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

EID: 0345422724     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(99)00040-3     Document Type: Review

References (48)

1. Wubbolts M.G., Witholt B. Selected industrial biotransformations. Montie T.C. Biotechnology Handbooks. 1998;271-329 Plenum, New York. A comprehensive review on industrial applications of the Pseudomonas genus as biocatalysts. This paper reviews literature until 1995.
2. Bommarius A.S., Schwarm M., Drauz K. Biocatalysis to amino acid based chiral pharmaceuticals - examples and perspectives. J Mol Cat B - Enzymatic. 5:1998;1-11. This paper describes the synthesis and applications of unnatural amino acids. Some examples from the Degussa portfolio concern are discussed and future trends in the markets for pharmaceutically active compounds are analysed.
3. Bruggink A., Roos E.C., de Vroom E. Penicillin acylase in the industrial production of β-lactam antibiotics. Org Proc Res Dev. 2:1998;128-133. Immobilized penicillin acylase is a biocatalyst suitable for the kinetically controlled synthesis of semi-synthetic antibiotics. Illustrative examples are given on how the limitations of the different systems are overcome.
4. Yagasaki M., Ozaki A. Industrial biotransformations for the production of D-amino acids. J Mol Cat B - Enzymatic. 4:1998;1-11. The industrial manufacture of D-alanine, D-glutamic acid and D-proline by biotransformations is reviewed.
5. McCoy M. Biocatalysis grows for drug synthesis. Chem Eng News. 77:1999;10-14.
6. Peterson M., Kiener A. Biocatalysis - preparation and functionalization of N-heterocycles. Green Chem. 1:1999;99-106. The advantages of biocatalysis in industrial transformations are highlighted using the examples of the preparation and modification of N-heterocycles.
7. Von Schriltz D.N. From the petrochemical industry to bioprocesses. Technol Chim. 18:1998;151-155.
8. Pantaleone D. Biotransformations: 'green' processes for the synthesis of chiral fine chemicals. Ager D. Handbook of Chiral Chemicals. 1999;245-286 Marcel Dekker, Inc, New York. A comprehensive review on industrial biotransformations in a very interesting book on chiral chemicals.
9. Fessner W.-D. Biocatalysis - from discovery to applications. Top Curr Chem. 200:1999;1-266. An edited book with contributions dealing with the synthetic utility of biotransformations.
10. Shanley A. Enzymes usher in a new era. Chem Eng. 1998;63-66.
11. Ogawa J., Shimizu S. Microbial enzymes: new industrial applications from traditional screening methods. Trends Biotechnol. 17:1999;13-21. This review discusses the industrial application of carbamoylase, nitrile hydratase, lactonase, proline hydroxylase and aldehyde reductase and gives a very comprehensive overview.
12. Stinson S.C. Counting on chiral drugs. Chem Eng News September. 21:1998;83-104.
13. Yamada H., Kobayashi M. Nitrile hydratase and its application to industrial production of acrylamide. Biosci Biotechnol Biochem. 60:1996;1391-1400.
14. Cheetham P. Case studies in applied biocatalysis - from ideas to products. Cabral J., Best D., Boross L., Tramper H. Applied Biocatalysis. 1994;47-108 Harwood Academic Publishers, London.
15. Tosa T., Shibatani T. Industrial application of immobilized biocatalysts in Japan. Ann NY Acad Sci. 750:1995;364-375.
16. Balkenhohl F., Ditrich K., Hauer B., Ladner W. Optisch aktive Amine durch Lipase-katalysierte Methoxyacetylierung. J Prakt Chem. 339:1997;381-384.
17. Stecher H., Faber K. Biocatalytic deracemization techniques: dynamic resolutions and stereoinversions. Synthesis. 1:1997;1-16.
18. Larsson A., Persson B.A., Bäckvall J.-E. Enzymatic resolution of alcohols coupled with ruthenium-catalyzed racemization of the substrate. Angew Chem Int Ed. 36:1997;1211-1212.
19. 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.
20. Um P.-J., Drueckhammer D. Dynamic enzymatic resolution of thioesters. J Am Chem Soc. 120:1998;5605-5610.
21. Hirohara H., Nishizawa M. Biochemical synthesis of several chemical inseticide intermediates and mechanism of action of relevant enzymes. Biosci Biotechnol Biochem. 62:1998;1-9. This paper describes the chemoenzymatic synthesis of several chiral intermediates. The most relevant point is the combination of enzymatic resolution processes with subsequent chemical transformation leading to the inversion of the undesired enantiomer.
22. Fessner W.-D. Enzyme mediated C-C bond formation. Curr Opin Chem Biol. 2:1998;85-97.
23. Mahmoudian M., Noble D., Drake C.S., Middleton R.F., Montgomery S., Piercey J.E., Ramlakhan D., Todd M., Dawson M.J. An efficient process for production of N-acetyl neuraminic acid using N-acetylneuraminic acid aldolase. Enzyme Microb Technol. 20:1997;393-400.
24. Kragl U., Kittelmann M., Ghisalba O., Wandrey C. N-Acetylneuraminic acid: from a rare chemical from natural sources to a multikilogram enzymatic synthesis for industrial application. Legoy M.-D., Thomas D. Enzyme Engineering. 1995;300-305 The New York Academy of Sciences, New York.
25. Collins A.M., Maslin C., Davies R.J. Scale-up of a chiral resolution using cross-linked enzyme crystals. Org Proc Res Dev. 2:1998;400-406.
26. Schmi A., Kollmer A., Mathys R.G., Witholt B. Developments toward large-scale bacterial bioprocesses in the presence of bulk amounts of organic solvents. Extremophiles. 2:1998;249-256.
27. Weuster-Botz D.H.E., Hartbrich A. Scale-up and application of a cyclone reactor for fermentation processes. Bioprocess Eng. 18:1998;433-438.
28. Li K., Frost J. Synthesis of vanillin from glucose. J Am Chem Soc. 120:1998;10545-10546.
29. Draths K.M., Knop D., Frost J.W. Shikimic acid and quinic acid: replacing isolation from plant sources with recombinant microbial biocatalysis. J Am Chem Soc. 121:1999;1603-1604.
30. Pal S., Nair V. Enzymatic synthesis of thymidine using bacterial whole cells and isolated purine nucleoside phosphorylase. Biocatalysis Biotransform. 15:1997;147-158.
31. Grifantini R., Galli G., Carpani G., Pratesi C., Frascotti G., Grandi G. Efficient conversion of 5-substituted hydantoins to D-amino acids using recombinant Escherichia coli strains. Microbiology. 144:1998;947-954.
32. 2 is performed via biotransformation, one of the organic dream reactions.
33. Wieser M., Yoshida T., Nagasawa T. Microbial synthesis of pyrrole-2-carboxylate by Bacillus mageterium PYR2910. Tetrahedron Lett. 39:1998;4309-4310.
34. +-specific formate dehydrogenase enables an easy approach for the NADPH cofactor regeneration utilizing formate.
35. Seelbach K., Riebel R., Hummel W., Kula M.-R., Tishkov V.I., Egorov A.M., Wandrey C., Kragl U. A novel, efficient regenerating method of NADPH using a new formate dehydrogenase. Tetrahedron Lett. 37:1996;1377-1380.
36. Rissom S., Schwarz-Linek U., Vogel M., Tishkov V., Kragl U. Synthesis of chiral ε-lactones in a two-enzyme system of cyclohexanone mono-oxygenase and formate dehydrogenase with integrated bubble-free aeration. Tetrahedron Asymmetry. 8:1997;2523-2526.
37. Liese A., Zelinski T., Kula M.-R., Kierkels H., Karutz M., Kragl U., Wandrey C. A novel reactor concept for the enzymatic reduction of poorly soluble ketones. J Mol Cat B - Enzymatic. 4:1998;91-99. Production of (S)-2-octanol in a continuously operated enzyme membrane reactor for over 4 months is described.
38. Zelinski T., Liese A., Wandrey C., Kula M.-R. Asymmetric reduction in aqueous media: enzymatic synthesis in cyclodextrin containing buffer. Tetrahedron Asymmetry. 10:1999;1681-1687. An increase in the solubility of substrates is achieved by addition of dimethylated cyclodextrins.
39. Shimizu S., Kataoka M., Kita K. Chiral alcohol synthesis with yeast carbonyl reductase. J Mol Cat B - Enzymatic. 5:1998;321-325.
40. Wada M., Kataoka M., Kawabata H., Yasohara Y., Kizaki N., Hasegawa J., Shimizu S. Purification and characterization of NADPH-dependent carbonyl reductase, involved in stereoselective reduction of ethyl 4-chloro-3-oxobutanoate, from Candida magnoliae. Biosci Biotechnol Biochem. 62:1998;167-169.
41. Yasohara Y., Kizaki N., Hasegawa J., Takahashi S., Wada M., Kataoka M., Shimizu S. Synthesis of optically active ethyl 4-chloro-3-hydroxybutanoate by microbial reduction. Appl Microb Biotechnol. 51:1999;847-851.
42. Iding H., Siegert P., Mesch K., Pohl M. Application of α-keto acid decarboxylases in biotransformations. Biochim Biophys Acta. 1385:1998;307-322.
43. Taylor S., Vu L., Begley T., Schörken U., Grolle S., Sprenger G., Bringer-Meyer S., Sahm H. Chemical and enzymatic synthesis of 1-deoxy-D-xylulose-5-phosphate. J Org Chem. 63:1998;2375-2377.
44. Sprenger G., Pohl M. Synthetic potential of thiamin diphosphate dependent enzymes. J Mol Cat B - Enzymatic. 6:1999;145-159. A comprehensive review on the applications of thiamin diphosphate-dependent enzymes.
45. Beliczey J, Kragl U, Liese A, Wandrey C, Coenen H, Hamacher K, Tierling T: Enzymatic synthesis of 3-fluoroneuraminic acid (5-acetamido-3,5-didesoxy-3-fluoro-D-glycero-D-galacto-nonulopyranosonic acid) and other 3,5-didesoxy-3-fluoro-nonu-lo-pyrano-sonic acid derivatives. US Patent 1998, 09/156322.
46. Azevedo WD, Ploeg JDV, Leisinger T, Kiener A, Heinzmann K, Gilligan T: Process for the production of L-alaninol and gamma-glutamyl isopropylamide and a microorganism strain of the genus Pseudomonas. World Patent Application 1999, WO9907199 A 19990218.
47. Bruhn H, Pohl M, Mesch K, Kula MR: Verfahren zur Herstellung von Acyloinen, dafür geeignete Pyruvatdecarboxylase sowie deren Herstellung und DNA-Sequenz des für diese kodierenden PDC-Gens. German Patent Application 1995, DE 195 23 269. [Title translation: Method for the production of acyloins, use of suitable pyruvate decarboxylase as well as its production and DNA sequence of the coding gene.].
48. Dünnwald T, Greiner L, Iding H, Liese A, Müller M, Pohl M: Stereoselektive Synthese von 2-Hydroxyketonen. German Patent Application 1999, DE 199 18 935 8. [Title translation: Stereoselective synthesis of 2-hydroxyketone.].