Enzymatic process for preparing N-acetylneuraminic acid

Details Enzymatic process for preparing N-acetylneuraminic acid Enzymatic process for preparing N-acetylneuraminic acid

1990-10-31

1991-12-10

Lilling, Herbert J.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Preparing compound containing saccharide radical

435 85, 435232, 435233, C12P 758, C12N 988, C12N 990, C07H 7033

Patent

active

050717502

ABSTRACT:
A process for obtaining N-acetylneuraminic acid from N-acetylglucosamine is disclosed. The process is carried out in a reactor which contains both N-acylglucosamine-2-epimerase (E.C. 5.1.3.8) which isomerizes GlcNAc into ManNAc, and N-acetylneuraminic acid pyruvate lyase (E.C. 4.1.3.3) which catalyzes the reaction of the resulting ManNAc with pyruvic acid to give Neu5Ac. GlcNAc and Pyr are fed into the reactor and Neu5Ac is obtained in the outflow. The process is preferably carried out continuously and in particular in an enzyme membrane reactor at pH 7.5 and 25.degree. C., especially using residence times of 0.2 to 10 h, and with an excess of GlcNAc in comparison with Pyr which is subsequently added if necessary. Epimerase and lyase are preferably present in the reactor in a ratio of activities which is equivalent to the reciprocal value of the quotient of the conversion rates.

REFERENCES:
patent: 4960701 (1990-10-01), Horiuchi et al.
Sadhamoy Ghosh and Saul Roseman, "The Sialic Acids, V.N-Acyl-D-Glucosamine 2-Epimerase", The Journal of Biological Chemistry, vol. 240, No. 4, Apr. 1965, pp. 1531-1536.
Asis Datta, "N-Acetylglucosamine 2-Epimerase from Hog Kidney", Carbohydrate Metabolism, vol. XLI, Part B, 1975, pp. 407-412.
Subramaniam Sabesan and James C. Paulson, "Combined Chemical and Enzymatic Synthesis of Sialyloligosaccharides and Characterization by 500 MHz .sup.1 H and .sup.13 C NMR Spectroscopy", J. Am. Chem. Soc., 108, 1986, pp. 2068-2080.
Roland Schauer, "Chemistry, Metabolism and Biological Functions of Sialic Acids", Advances in Carbohydrate Chemistry and Biochemistry, vol. 40, 1982, pp. 131-234.
Donald G. Comb and Saul Roseman, "The Structure and Enzymatic Synthesis of N-Acetylneuraminic Acid", Journal of Biological Chemistry, vol. 235, No. 9, Sep. 1960, pp. 2529-2537.
Mahn-Joo Kim, William J. Hennen, H. Marcel Sweers, and Chi-Huey Wong, "Enzymes in Carbohydrate Synthesis: N-Acetylneuraminic Acid Aldolase Catalyzed Reactions and Preparation of N-Acetyl-2-deoxy-D-neuraminic Acid Derivatives", J. Am. Chem. Soc., 110, 1988, 6481-6486.
Claudine Auge, Benedicte Bouxom, Bertrand Cavaye and Christine Gautheron, "Scope and Limitations of the Aldol Condensation Catalyzed by Immobilized Acylneuraminate Pyravute Lyase", Tetrahedron Letters, vol. 30, No. 17, 1989, pp. 2217-2220.

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