Process for isolating and purifying nucleotide-activated sugars

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

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536 172, 536 179, 536 265, 536 285, 536 553, C07H 1906, C07H 1916

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058115390

ABSTRACT:
The present invention relates to an improved process for isolating and purifying sugar nucleotides, in particular cytidine monophosphate-activated N-acetylneuraminic acid (CMP-Nana), from biological sources. The sugar nucleotides can be obtained from a sugar nucleotide-containing solution, which has been freed of proteins by alcoholic precipitation, by means of an improved column-chromatographic method which uses silica gel as the stationary phase, and at a purity level which requires only a subsequent desalting step to obtain a substantially pure product.

REFERENCES:
Comb et al., "The Sialic Acids: Isolation of Cytindine 5'-Monophospho-N-Acetylneuraminic Acid From Escherichia Coli K-235", Journal of Biol. Chem., vol. 241, No. 23, (1996) pp. 5637-5642.
Liu et al., "Overproduction of CMP-Sialic Acid Synthetase for Organic Synthesis", J. Am. Chem. Soc., vol. 114, (1992) pp. 3901-3910.
Shoyab et al., "Purification and Properties of the CMP-N-Acetylneuraminic Acid Synthesizing Enzyme From Sheep Brain", Journal of Neurochem., vol. 11, (1964), pp. 639-646.
D, Van Den Eijnden et al., "A Convenient Method for the Preparation of Cytidine 5'-Monophospho-N-Acetylneuraminic Acid,", Hoppe-Seyler's Z. Physiol. Chem. Bd. 353, (1972) pp. 1817-1820.
Auge et al., "An Efficient Synthesis of Cytidine Monophospho-Sialic Acids with Four Immobilized Enzymes", Tetrahedron Letters, vol. 29, No. 7, (1988), pp. 789-790.
Higa et al., "Sialylation of Glycoprotein Oligosaccharides with N-Acetyl-, N-Glycolyl-, and N-o-Diacetylneuraminic Acids", J. Biol. Chem., vol. 260, No. 15, (1985) pp. 8838-8849.
Kittelmann et al., "Preparative Enzymatic Synthesis of Activated Neuraminic Acid by Using a Microbial Enzyme", Annals New York Acad. Sci., vol. 672, (1992), pp. 444-450.
Makino et al., "Chemical Synthesis of Cytidine-5'-Monophosphono-N-Acetylneuraminic Acid (CMP-Neu5Ac)",Tetrahedron Letters, vol. 34, No. 17, (1993), pp. 2775-2778.
Martin et al., Convenient Chemical Synthesis of CMP-N-Acetylneuraminate (CMP-Neu-5-Ac) Tetrahedron Letters, vol. 34, No. 11, (1993) pp. 1765-1768.
Ikeda et al., "Synthesis of Sialic Acid-Containing Nucleotide Sugars: CMP-Sialic Acid Analogs", Carbohydrate Res., vol. 224, (1992), pp. 123-131.
Ichikawa et al., "Efficient Chemical Synthesis of GDP-Fucose", Journal of Org. Chem., vol. 57, (1992), pp. 2943-2946.
Adelhorst et al., "Large-scale Synthesis of B-L-Fucopyranosyl Phosphate and the Preparation GDP-B-L-Fucose", Carbohydrate Res., vol. 242, (1993), pp. 69-76.
Schmidt et al., Stereospecific Synthesis of .alpha.-and .beta.-L-Fucopyranosyl Phosphates and of GDP-Fucose via Trichloroachetimidate, Ann. Chem., (1991), pp. 121-124.
Shames et al., "CMP-N-Acetylneuram. Acid. Synth. of Escheri. Coli: Hgh. Lev. Exp., Purif. & Use in Enzym. Synth. CMP-N-Acetylneuram. Acid & CMP-Neuram. Acid Deriv.", Glycobio., vol. 1, No. 2, (1991), pp. 187-191.
Heidlas et al., "Gram-Scale Synthesis of Uridine 5'-Diphospho-N-Acetylglucosamine: Comparison of Enzymatic and Chemical Routes", The Journal of Organic Chemistry, vol. 57, No. 1, (1992), pp. 146-151.
Heidlas et al., "Nucleoside Phosphate Sugars: Syntheses on Practical Scales for Use as Reagents in the Enzymatic Prep. of Oligosaccharides and Glycoconjugates", Acc. Chem Res., vol. 25, (1992), pp. 307-314.
Comb et al., "Isolation of Cytidine-5'-Monophospho-N-Acetylneuraminic Acid", Communications to the Editor, vol. 81, (1959), pp. 5513-5514.
Stiller et al., "Enzymatic Synthesis of B-L-Fucose-1-Phosphate and GDP-Fucose", Ann Chem., (1992) pp. 467-471.
Simon et al., Conv. Synth. of Cytid. 5'-Triphosp., Buanosine 5'-Triphos., & Their Use in Prep. of UDP-Glucose, UDP-Glucuronic Acid, & GDP-Mannose, J. Org. Chem. vol. 55, (1990), pp. 1834-1841.
Wong et al., "Regen. Sugar Nucleo. Enzym. Oligosaccharide Synth.: Use Gal-1-Phosphate Uridlytrans. in the Regen. UDP-Galactose, UDP-2-Deoxygalac., UDP-Galactos.", J. Org. Chem., vol. 57, (1992), pp. 4343-4344.
Pallanca et al., "Chemo-Enzymic Synthesis of Guanosine 5'-Diphosphomannose (GDP-Mannose) and Selected Analogues", Journal Chem. Soc. Perkin Trans. 1, (1993), pp. 3017-3022.
Petrie et al., "A High-Performance Liquid Chromatography Method for the Assay of Cytdine Monophosphate-Sialic Acid Synthetase", Ananlytical Biochem., vol. 131, (1983), pp. 153-159.

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