Towards novel processes for the fine-chemical and pharmaceutical industries

Current Opinion in Biotechnology

Volumn 13, Issue 4, 2002, Pages 352-358

  Huisman, Gjalt W ^a   Gray, David ^a  

^a R and D Project Development and Management   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXOGLUTARIC ACID; AMMONIUM CHLORIDE; ATORVASTATIN; CLARITHROMYCIN; CYTOCHROME P450; ERYTHROMYCIN; HEXOKINASE; NICOTINAMIDE; OMEPRAZOLE; PHOSPHOGLUCOMUTASE; PHYTASE; PRAVASTATIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; SIMVASTATIN; URIDINE DIPHOSPHATE GALACTOSE; URIDINE TRIPHOSPHATE GLUCOSE 1 PHOSPHATE URIDYLYLTRANSFERASE;

BIOCATALYST; BIOTECHNOLOGY; CATALYSIS; CHEMICAL INDUSTRY; DRUG INDUSTRY; DRUG MARKETING; ECONOMICS; ENANTIOSELECTIVITY; ENGINEERING; ENZYME SYNTHESIS; MOLECULE; PRIORITY JOURNAL; REVIEW; STEREOCHEMISTRY;

EID: 0036669389     PISSN: 09581669     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0958-1669(02)00335-X     Document Type: Review

References (36)

1. Fischer E. Einfluss der configuration auf die wirkung der enzyme. Ber Dt Chem Ges. 27:1894;2985-2993.
2. Rozzel D.J. Commercial scale biocatalysis: myths and realities. Bioorg Med Chem. 7:1999;2253-2261.
3. Powell K.A., Ramer S.W., del Cardayre S.B., Stemmer W.P.C., Tobin M.B., Longchamp P.F., Huisman G.W. Directed evolution and biocatalysis. Angew Chem Int Ed Engl. 40:2001;3948-3959.
4. Powell KA: Industrial biocatalysis - the American view from industry. In Proceedings of Enzyme Engineering XVI, Oct 7-12, 2001, Postdam Germany.
5. Schmid A., Dordick J.S., Hauer B., Kiener A., Wubbolts M., Witholt B. Industrial biocatalysis today and tomorrow. Nature. 409:2001;258-268. An excellent review that provides an industrial perspective on the use of biocatalysis.
6. Burton S.G., Cowan D.A., Woodley J.M. The search for the ideal biocatalyst. Nat Biotechnol. 20:2002;37-45. A detailed and well-written perspective on how modern technology can aid in the design of novel processes by delivering the optimal catalyst.
7. May S.W. Applications of oxidoreductases. Curr Opin Biotechnol. 10:1999;370-375.
8. Wichman R., Wandrey C. Continuous enzymatic transformation in an enzyme membrane reactor with simultaneous NAD(H) regeneration. Biotech Bioeng. 23:1981;2789-2802.
9. Kataoka M., Sri Rohani L.P., Wada M., Kita K., Yanase H., Urabe I., Shimizu S. Escherichia coli transformant expressing the glucose dehydrogenase gene from Bacillus megaterium as a cofactor regenerator in a chiral alcohol production system. Biosci Biotechnol Biochem. 62:1998;167-169.
10. Asada H., Itoh T., Kodera Y., Matsushima A., Hiroto M., Nishimura H., Inada Y. Glutamate synthesis via photoreduction of NADP+ by photostable chlorophyllide coupled with polyethylene-glycol. Biotech Bioeng. 76:2001;86-90.
11. Miles C.S., Ost T.W., Noble M.A., Munro A.W., Chapman S.K. Protein engineering of cytochromes P-450. Biochim Biophys Acta. 1543:2000;383-407.
12. Reipa V., Mayhew M.P., Vilker V.L. A direct electrode-driven P450 cycle for biocatalysis. Proc Natl Acad Sci USA. 94:1997;13554-13558.
13. Schwaneberg U., Appel D., Schmitt J., Schmid R.D. P450 in biotechnology: zinc driven omega-hydroxylation of p-nitrophenoxydodecanoic acid using P450 BM-3 F87A as a catalyst. J Biotechnol. 84:2000;249-257. Zinc-dustand a mediator are used to replace NADPH in cytochrome P450 monooxygenase-driven reactions.
14. Mayhew M.P., Reipa V., Holden M.J., Vilker V. Improving the cytochrome P450 enzyme system for electrode-driven biocatalysis of styrene epoxidation. Biotechnol Prog. 16:2000;610-616.
15. Joo H., Lin Z., Arnold F.H. Laboratory evolution of peroxide-mediated cytochrome P450 hydroxylation. Nature. 399:1999;670-673. The use of the hydrogen-peroxide shunt is described for cytochrome P450 monooxygenases. The improvement in stability of these enzymes towards this reactive molecule by directed evolution is described.
16. Appel D., Lutz-Wahl S., Fischer P., Schwaneberg U., Schmid R.D. A P450 BM-3 mutant hydroxylates alkanes, cycloalkanes, arenes and heteroarenes. J Biotechnol. 88:2001;167-171.
17. Ma X., Stockigt J. High yielding one-pot enzyme catalyzed synthesis of UDP-glucose in gram scales. Carbohydr Res. 333:2001;159-163.
18. Hokke C.H., Zervosen A., Elling L., Joziasse D.H., van den Eijnden D.H. One-pot enzymatic synthesis of the Galα1→3Galβ1→4GlcNAc sequence with in situ UDP-Gal regeneration. Glycoconj J. 13:1996;687-692.
19. Schoevaart R., van Rantwijk F., Sheldon R.A. A four-step enzymatic cascade for the one-pot synthesis of non-natural carbohydrates from glycerol. J Org Chem. 65:2000;6940-6943.
20. van der Velde F., Konemann L., van Rantwijk F., Sheldon R.A. The rational design of semisynthetic peroxidases. Biotechnol Bioeng. 67:2000;87-96.
21. Cherry J.R., Lamsa M.H., Schneider P., Vind J., Svendsen A., Jones A., Pedersen A.H. Directed evolution of a fungal peroxidase. Nat Biotechnol. 17:1999;379-384.
22. Huerta F.F., Backvall J.-E. Enantioselective synthesis of β-hydroxyacid derivatives via a one-pot aldol reaction-dynamic kinetic resolution. Org Lett. 3:2001;1209-1212.
23. Huerta F.F., Laxmi Y.R.S., Backvall J.-E. Dynamic kinetic resolution of α-hydroxyacid esters. Org Lett. 2:2000;1037-1040.
24. Kim M.-J., Choi Y.K., Choi M.Y., Kim M.J., Park J. Lipase/ruthenium-catalyzed dynamic kinetic resolution of hydroxy acids, diols and hydroxy aldehydes protected with a bulky group. J Org Chem. 66:2001;4736-4738.
25. Choi Y.K., Suh J.H., Lee D., Lim I.T., Jung J.Y., Kim M.-J. Dynamic resolution of acyclic allylic acetates using lipase and palladium. J Org Chem. 64:1999;8423-8424.
26. Jung H.M., Koh J.H., Kim M.J., Park J. Practical ruthenium/lipase-catalyzed asymmetric transformations of ketones and enol acetates to chiral acetates. Org Lett. 2:2000;2487-2490.
27. Choi Y.K., Kim M.J., Ahn Y., Kim M.-J. Lipase/palladium-catalyzed asymmetric transformations of ketoximes to optically active amines. Org Lett. 3:2001;4099-4101. The field of transition-metal mediated dynamic kinetic resolution is growing rapidly. This paper describes its use for the production of amines.
28. Bailey J.E. Lessons from metabolic engineering for functional genomics and drug discovery. Nat Biotechnol. 17:1999;616-618.
29. Tobin M.B., Gustafsson C., Huisman G.W. Directed evolution: the 'rational' basis for 'irrational' design. Curr Opin Struct Biol. 10:2000;421-427.
30. Zhang Y.X., Perry K., Vinci V.A., Powell K., Stemmer W.P., del Cardayre S.B. Genome shuffling leads to rapid phenotypic improvement in bacteria. Nature. 415:2002;644-646. Shuffling at the genomic level led to the generation of tylosin-production strains in time frames less than 10% of that of traditional strain improvement procedures.
31. Ykema A, Streekstra H, Luiten R, Gijsbertus M: Statin Production by Fermentation. PCT WO9910499, 4 March 1999. Bacterialgenes were isolated and expressed in a fungus with the aim of simplifying the pravastatin manufacturing process from a two-stage fermentation to a single fermentation. Described product titers need to be improved for commercialization.
32. Selifonov SA, Newman LM: Preparation of 4-hydroxy-3[H]-furanones. PCT WO0192247.
33. Fong S., Machajewski T.D., Mak C.C., Wong C. Directed evolution of D-2-keto-3-deoxy-6-phosphogluconate aldolase to new variants for the efficient synthesis of D- and L-sugars. Chem Biol. 7:2000;873-883. DNA shuffling is used to generate new enzymes that act on non-activated substrates. This broadening of enzyme substrate specificities increases the potential utility of biocatalysts for commercial applications.
34. Berry A, Burlingame RP, Millis JR: Process and Materials for Production of Glucosamine. PCT WO0004182; 30 May, 2001.
35. Patel R.N. Biocatalytic synthesis of intermediates for the synthesis of chiral drug substances. Curr Opin Biotechnol. 12:2001;587-604.
36. Zaks A. Industrial biocatalysis. Curr Opin Chem Biol. 5:2001;130-136.