Characterization of the chemoenzymatic synthesis of N-acetyl-D-neuraminic acid (Neu5Ac)

Biotechnology Progress

Volumn 12, Issue 6, 1996, Pages 758-763

  Blayer, Simone ^a   Woodley, John M ^a   Lilly, Malcolm D ^a   Dawson, Michael J ^b  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCONVERSION; BIOSYNTHESIS; CATALYSIS; COLIFORM BACTERIA; CONDENSATION REACTIONS; ENZYMES;

ALDOLASE CATALYZED CONDENSATION; BASE CATALYZED EPIMERIZATION; BIOTRANSFORMATION PROCESS DESIGN; CHEMOENZYMATIC SYNTHESIS;

DRUG PRODUCTS;

EID: 0030293657     PISSN: 87567938     EISSN: None     Source Type: Journal    
DOI: 10.1021/bp9600647     Document Type: Article

References (35)

1. Aisaka, K.; Igarashi, A.; Yamaguchi, K.; Uwajima, T. Purification, crystallisation and characterisation of N-acetylneurami-nate lyase from Escherichia coll. Biochem. J. 1991, 276, 541-546.
2. Auge, C.; David, S.; Gautheron, C. Synthesis with immobilized enzyme of the most important sialic acid. Tetrahedron Lett. 1984, 25, 4663-4664.
3. Barker, S. A.; Jones, R. G.; Somers, P. J. Improvements in the production and isolation of colominic acid. Carbohydrate Res. 1967, 3, 369-376.
4. Cooney, C. L. Bioreactors: design and operation. Science 1983, 219, 728-733.
5. Dawson, M. J.; Noble, D.; Mahmoudian, M. Process for the Preparation of N-Acetylneuraminic Acid. World Patent WO 94/29476, 1994.
6. Dawson, R. M. C.; Eliott, D. C.; Eliott, W. H.; Jones, A. M. Data for Biochemical Research; Clarendon Press: Oxford, U.K., 1993; p 310.
7. Fitz, W.; Schwark, J. R.; Wong, C. H. Aldotetroses and C(3)-modified aldohexoses as substrates for N-acetylneuraminic acid aldolase: a model for the explanation of the normal and the inversed stereoselectivity. J. Org. Chem. 1995, 60, 3663-3670.
8. Freeman, A.; Woodley, J. M.; Lilly, M. D. In situ product removal as a tool for bioprocessing. Bio / Technology 1993, 11, 1007-1012.
9. Ghosh, S.; Roseman, S. The sialic acids V. N-Acyl-D-glucosamine 2-epimerase. J. Biol. Chem. 1965, 240, 1531-1536.
10. Gottschalk, A. 2-Carboxypyrrole: its preparation from and its precursor in mucoproteins. Biochem. J. 1955, 61, 298-307.
11. Izard, T.; Lawrence, M. C.; Malby, R. L.; Lilley, G. G.; Colman, P. M. The three-dimensional structure of N-acetylneuraminate lyase from Escherichia coli. Structure 1994, 2, 361-369.
12. Kim, M. J.; Henne, W. J.; Sweers, H. M.; Wong, C.-H. Enzymes in carbohydrate synthesis: N-acetylneuraminic acid aldolase catalysed reactions in preparation of N-acetyl-2-deoxy-D-neuraminic acid derivatives. J. Am. Chem. Soc. 1988, 110, 6481-6484.
13. Kragl, U.; Appel, P.; Gygax, D.; Ghisalba, O.; Wandrey, C. Aldolases for use in carbohydrate synthesis: enzymatic reaction engineering as a tool for process optimization. In Biochemical Engineering for 2001; Furusaki, S., Endo, I., Matsuno, R., Eds.; Springer-Verlag: New York, 1992; pp 84-87.
14. Kragl, U. Reactionstechnik Biocatalytischer Prozesse am Beispiel der Kontinuierlichen Enzymatischen Synthese. Ph.D. Dissertation, Forschunszentrum Julich, 1992.
15. 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. Ann. N. Y. Acad. Sci. 1995, 750, 300-305.
16. Kuhn, R.; Baschang, G. Amino sugar syntheses. Synthesis of lactaminic [N-acetylneuraminic] acid. Liebigs Ann. Chem. 1962, 659, 156-163.
17. Lee, Y. C. High performance anion-exchange chromatography for carbohydrate analysis. Anal. Biochem. 1990, 189, 151-162.
18. Lin, C.-H.; Sugai, T.; Halcomb, R. L.; Ichikawa, Y.; Wong, C.-H. Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides. J. Am. Chem. Soc. 1992, 114, 10138-10145.
19. Mahmoudian, M.; Noble, D.; Drake, C. S.; Middleton, F. B.; Montgomery, D. S.; Piercey, J. E.; Ramlakhan, D.; Todd, M.; Dawson, M. J. An efficient process for production of N-acetylneuraminic acid using N-acetylneuraminic acid aldolase. Enzyme Microb. Technol., in press.
20. Margolin, A. L. Enzymes in the synthesis of chiral drugs. Enzyme Microb. Technol. 1993, 15, 266-280.
21. Roseman, S.; Comb, D. G. The hexosamine moiety of N-acetylneuraminic acid (sialic acid). J. Am. Chem. Soc. 1958, 80, 3166-3167.
22. Roy, R.; Boratynski, J. Production of N-glycolylneuraminic acid derived by enzymatic catalysis. Biotechnol. Lett. 1990, 12, 347-352.
23. Schauer, R. Chemistry and biology of the acylneuraminic acids. Angew. Chem., Int. Ed. Engl. 1973, 12, 127-138.
24. Schauer, R. Characterisation of sialic acid. Methods Enzymol. 1978, 50c, 64-89.
25. Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. Synthesis of CMP-Neu5Ac from N-acetylglucosamine: generation of CTP from CMP using adenylate kinase. J. Am. Chem. Soc. 1988, 110, 7159-7163.
26. Stinson, S. C. Chiral drugs. Chem. Eng. News 1995, 41, 44-74.
27. Sugai, T.; Kuboki, A.; Hiramatsu, S.; Okazaki, H.; Ohta, H. Improved enzymatic procedure for a preparative scale synthesis of sialic acid and KDN. Bull. Chem. Soc. Jpn. 1995, 68, 3581-3589.
28. Tsukada, Y.; Ohta, Y. Process for producing N-acetylneuraminic acid. European patent 0 578825 Al, World patent WO 93/ 15214, 1994.
29. Uchida, Y.; Tsukada, Y.; Sugimori, T. Purification and properties of N-acetylneuraminate lyase from Escherichia coli. J. Biochem. 1984, 96, 507-522.
30. Von Itzstein, M.; Wu, W. Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Van Phan, T.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryan, D. M.; Woods, J. M.; Bethell, R. C.; Hotham, V. J.; Cameron, J. M.; Penn, C. R. Rational design of potent sialidase-based inhibitors of influenza virus replication. Nature 1993, 363, 418-423.
31. Wheelwright, S. M. Designing downstream processes for largescale protein purification. Bio / Technology 1989, 5, 789-793.
32. Woodley, J. M.; Lilly, M. D. Process engineering of two-liquid phase biocatalysis. In Biocatalysis in Non-Conventional Media. Tramper, J., Vermüe, M. H., Beeftink, H. H., von Stockar, U., Eds.; Elsevier Science Publisher B.V.: Amsterdam, 1992; pp 147-154.
33. Woodley, J. M.; Lilly, M. D. Biotransformation reactor selection and operation. In Applied Biocatalysis; Cabrai, J. M. S., Best, D., Boross, L., Tramper, J., Eds.; Harwood Academic: Chur, Switzerland, 1994; pp 371-393.
34. Woodley, J. M.; Lilly, M. D. Select and design. Chem. Eng. (Rugby, Engl.) 1996, 611, 28-30.
35. Woodley, J. M.; Titchener-Hooker, N. J. The use of windows of operation as a bioprocess design tool. Bioprocess Eng. 1996, 14, 263-268.