Enzymatic synthesis of cytidine 5′-monophospho-N-acetylneuraminic acid

Bioscience, Biotechnology and Biochemistry

Volumn 69, Issue 10, 2005, Pages 1944-1950

  Hamamoto, Tomoki ^a   Takeda, So ^a   Noguchi, Toshitada ^a  

^a YAMASA CORPORATION   (Japan)

Author keywords

Cytidine 5 monophospho N acetylneuraminic acid (CMP NeuAc); N acetylglucosamine (GlcNAc) 6 P 2 epimerase; N acetylneuraminic acid; NeuAc synthetase

Indexed keywords

BIOSYNTHESIS; CELLS; CLONING; ESCHERICHIA COLI; GENES; GLUCOSE; ORGANIC ACIDS; SYNTHESIS (CHEMICAL); YEAST;

GENE ENCODING; N-ACETYLGLUCOSAMINE (GLCNAC) 6-P 2-EPIMERASE; N-ACETYLNEURAMINIC ACID; YEAST CELLS;

ENZYMES;

ACYLNEURAMINATE CYTIDYLYLTRANSFERASE; BACTERIAL PROTEIN; CYTIDINE PHOSPHATE; CYTIDINE PHOSPHATE N ACETYLNEURAMINIC ACID; EPIMERASE; N ACETYLGLUCOSAMINE; N ACYLGLUCOSAMINE 6 PHOSPHATE 2 EPIMERASE; N-ACYLGLUCOSAMINE-6-PHOSPHATE 2-EPIMERASE; VIRUS PROTEIN;

ARTICLE; CHEMISTRY; ESCHERICHIA COLI; GENETICS; METABOLISM; SYNTHESIS; YEAST;

ACETYLGLUCOSAMINE; BACTERIAL PROTEINS; CARBOHYDRATE EPIMERASES; CYTIDINE MONOPHOSPHATE; CYTIDINE MONOPHOSPHATE N-ACETYLNEURAMINIC ACID; ESCHERICHIA COLI; N-ACYLNEURAMINATE CYTIDYLYLTRANSFERASE; VIRAL PROTEINS; YEASTS;

CAMPYLOBACTER JEJUNI; ESCHERICHIA COLI; HAEMOPHILUS INFLUENZAE;

EID: 27644582795     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.69.1944     Document Type: Article

References (34)

1. Schauer, R., Chemistry, metabolism, and biological function of sialic acids. Adv. Carbohydr. Chem. Biochem., 40, 131-234 (1982).
2. Schauer, R., "Sialic Acids: Chemistry, Metabolism, and Function", ed. Schauer, R., Springer-Verlag, New York, pp. 263-305 (1982).
3. Harduin-Lepers, A., Recchi, M.-A., and Delannoy, P., 1994, the year of sialyltransferase. Glycobiology, 5, 741-758 (1995).
4. Weisgerber, C., Hansen, A., and Frosch, M., Complete nucleotide and deduced protein sequence of CMP-NeuAc: poly-α-2,8 sialosyl sialyltransferase of Escherichia coli. Glycobiology, 1, 357-365 (1991).
5. Frosch, M., Edwards, U., Bousset, K., Krausse, B., and Weisgerber, C., Evidence for a common molecular origin of the capsule gene loci in Gram-negative bacteria expressing group II capsular polysaccharaides. Mol. Microbiol., 5, 1251-1263 (1991).
6. Gilbert, M., Watson, D. C., Cunningham, A.-M., Jennings, M. P., Young, N. M., and Wakarchuk, W. W., Cloning of the liposaccharaide a-2,3- sialyltransferase from the bacterial pathogens Neisseria meningitidis and Neisseria gonorrhoeae. J. Biol. Chem., 271, 28271-28276 (1996).
7. Gilbert, M., Bayer, R., Cunningham, A.-M., DeFrees, S., Gao, Y., Watson, D. C., Young, N. M., and Wakarchuk, W. W., The synthesis of sialylated oligosaccharides using a CMP-Neu5Ac synthetase/sialyltransferase fusion. Nat. Biotechnol., 16, 769-772 (1998).
8. Uchida, Y., Tsukada, Y., and Sugimori, T., Improved microbial production of colominic acid, a homopolymer of N-acetyl-D-neuraminic acid. Agric. Biol. Chem., 37, 2105-2110 (1973).
9. Juneja, L. R., Koketsu, M., Nishimoto, K., Kim, M., Yamamoto, T., and Itoh, T., Large-scale preparation of sialic acid from chalaza and egg-yolk membrane. Carbohydr. Res., 214, 179-186 (1991).
10. Comb, D. G., and Roseman, S., The structure and enzymatic synthesis of N-acetyl-D-neuraminic acid. J. Biol. Chem., 235, 2529-2537 (1960).
11. Auge, C., David, S., and Gautheron, C., Synthesis and immobilized enzyme of the most important sialic acid. Tetrahedron Lett., 25, 4663-4664 (1984).
12. Kim, M., Hennen, W. A. J., Sweers, H. M., and Wong, C. H., Enzymes in carbohydrate synthesis: N-acetyl-D-neuraminic acid aldolase-catalyzed reactions and preparations of N-acetyl-2-deoxy-D-neuraminic acid derivatives. J. Am. Chem. Soc., 110, 6481-6484 (1988).
13. Maru, I., Ohnishi, J., Ohta, Y., and Tsukada, Y., Simple and large-scale production of N-acetylneuraminic acid from N-acetyl-D-glucosamine and pyruvate using N-acyl-D-glucosamine 2-epimerase and N-acetylneuraminic lyase. Carbohyr. Res., 306, 575-578 (1998).
14. Tabata, K., Koizumi, S., Endo, T., and Ozaki, A., Production of N-acetyl-D-neuraminic acid by coupling bacteria expressing N-acetyl-D- glucosamine 2-epimerase and N-acetyl-D-neuraminic acid synthetase. Enz. Microbial. Technol., 30, 327-333 (2002).
15. Shames, S. L., Simon, E. S., Christopher, C. W., Schmid, W., Whitesides, G. M., and Yang, L. L., CMP-N-acetylneuraminic acid synthetase of Escherichia coli: high level expression, purification, and use in the enzymatic synthesis of CMP-N-acetylneuraminic acid and CMP-neuraminic acid derivatives. Glycobiology, 1, 187-191 (1991).
16. Shen, G.-J., Liu, J. L.-C., and Wong, C.-H., Cloning and overexpression of a tagged CMP-N-acetylneuraminic acid synthetase from E. coli using a lambda phage system and application of the enzyme to the synthesis of CMP-N-acetylneuraminic acid. Biocatalysis, 6, 31-42 (1992).
17. Kittelmann, M., Klein, T., Kragl, U., Wandrey, C., and Ghisalba, O., CMP-N-acetyl neuraminic-acid synthetase from Escherichia coli: fermentative production and application for the preparative synthesis of CMP-neuraminic acid. Appl. Microbiol. Biotechnol., 44, 59-67 (1995).
18. Simon, E. S., Bednarski, M. D., and Whitesides, G. M., Synthesis of CMP-NeuAc from N-acetylglucosamine: generation of CTP from CMP using adenylate kinase. J. Am. Chem. Soc., 110, 7159-7163 (1988).
19. Endo, T., Koizumi, S., Tabata, K., and Ozaki, A., Large-scale production of CMP-NeuAc and sialylated oligosaccharides through bacterial coupling. Appl. Microbiol. Biotechnol., 53, 257-261 (2000).
20. Okuyama, K., Hamamoto, T., Ishige, K., Takenouchi, K., and Noguchi, T., An efficient method for production of uridine 5′-diphosphate-N- acetylglucosamine. Biosci. Biotechnol. Biochem., 64, 386-392 (2000).
21. Messing, J., New M13 vectors for cloning. In "Methods in Enzymol" Vol. 101, eds. Wu, R., Grossman, L., and Moldave, K., Academic Press, New York, pp. 3-11 (1983).
22. Backmann, B. J., Derivation and genotypes of some mutant derivatives of Escherichia coli K-12. In "Escherichia coli and Salmonella typhimurium, Cellular and Molecular Biology", eds. Neidhardt, F. C., Ingraham, J., Low, K., Magasanik, B., Scahechter, M., and Umbargar, H., ASM Press, Washington D.C., pp. 1190-1219 (1987).
23. Aman, E., Ochs, B., and Abel, K. J., Tightly regulated tac promoter vectors useful for the expression of unfused and fused protein in Escherichia coli. Gene, 69, 301-315 (1988).
24. Molecullar cloning, a laboratory manual, Second ed., eds. Sambrook, J., Fritsch, E. F., and Maniatis, T., Cold Spring Harbor Laboratory Press, New York (1989).
25. Fleischmann, R. D., Adams, M. D., White, O., Clayton, R. A., Kirkness, E. F., Kerlavage, A. R., Bult, C. J., Tomb, J.-F., Dougherty, B. A., Merrick, J. M., McKenney, K., Sutton, G. G., FitzHugh, W., Fields, C. A., Gocayne, J. D., Scott, J. D., Shirley, R., Liu, L. I., Glodek, A., Kelley, J. M., Weidman, J. F., Phillips, C. A., Spriggs, T., Hedblom, E., Cotton, M. D., Utterback, T., Hanna, M. C., Nguyen, D. T., Saudek, D. M., Brandon, R. C., Fine, L. D., Fritchman, J. L., Fuhrmann, J. L., Geoghagen, N. S., Gnehm, C. L., McDonald, L. A., Small, K. V., Fraser, C. M., Smith, H. O., and Venter, J. C., Whole-genome random sequencing and assembly of Haemophilus influenzae Rd. Science, 269, 496-512 (1995).
26. Parkhill, J., Wren, B. W., Mungall, K., Ketly, J. M., Churcher, C., Basham, D., Chillingworth, T., Davies, R. M., Feltwell, T., Holroyd, S., Jageles, K., Karlyshev, A. V., Molue, S., Pallen, M. J., Penn, C. W., Quail, M. A., Rajandream, M. A., Rutherford, K. M., van Vliet, A. H., Whitehead, S., and Barrell, B. G., The genome sequence of the food-borne pathogen Campylobacter jejuni reveals hypervariable sequences. Nature, 403, 665-668 (2000).
27. Ishige, K., Hamamoto, T., Shiba, T., and Noguchi, T., Novel method for enzymatic synthesis of CMP-NeuAc. Biosci. Biotechnol. Biochem., 65, 1736-1740 (2001).
28. Lee, Y. C., High-performance anion-exchange chromatography for carbohydrate analysis. Anal. Biochem., 189, 151-162 (1990).
29. Postma, P. W., and Lengeler, J., Phosphoenolpyruvate carbohydrate phosphotransferase system of bacteria. Microbiol. Rev., 49, 232-269 (1985).
30. Man complex of Escherichia coli. J. Biol. Chem., 260, 15495-15503 (1985).
31. Plumbridge, J., and Vimr, E., Convergent pathways for utilization of the amino sugars N-acetylglucosamine, N-acetylmannosamine, and N-acetylneuraminic acid by Escherichia coli. J. Bacteriol., 181, 47-54 (1999).
32. Linton, D., Karlyshev, A. V., Hitchen, P. G., Morris, H. R., Dell, A., Gregson, N. A., and Wren, B. W., Multiple N-acetyl neuraminic acid synthetase (neuB) genes in Campylobacter jejuni: identification and characterization of the gene involved in sialylation of lipo-oligosaccharide. Mol. Microbiol., 35, 1120-1134 (2000).
33. Ichikawa, Y., Lin, Y.-C., Dumas, D. P., Shen, G. J., Eduaro, G.-J., Mark, A. W., Bayer, R., Ketcham, C., Walker, L. E., Paulson, J. C., and Wong, C.-H., Chemical-enzymatic synthesis and conformational analysis of Sialyl Lewis X and derivatatives. J. Am. Chem. Soc., 114, 9283-9298 (1992).
34. Goldie, H., and Medina, V., Physical and genetic analysis of the phosphoenolpyruvate carboxykinase (pckA) locus from Escherichia coli K12. Mol. Gen. Genet., 220, 191-196 (1990).