Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1993-12-22
1996-06-18
Woodward, Michael P.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 187, 536123, 536124, 436518, 436532, 436543, 436544, 436545, 436546, C07H 504, C07G 1700, G01N 33543, G01N 33534
Patent
active
055279015
ABSTRACT:
The stereochemistry of sialylation of an acceptor saccharide to obtain an .alpha. (2-3) or .alpha. (2-6) linkage is controlled to favor the .alpha. anomer by use of an aromatic ester of the sialyl reagent. The resulting intermediate .alpha. (2-3) and .alpha. (2-6) sialylated intermediate disaccharide blocks are useful in the synthesis of antigenic substances which can be used to raise antibodies useful in diagnosis and therapy, and can themselves be used as reagents in various applications. The preparation of the tetrasaccharide antigens corresponding to the 19-9 and sialyl-X antigens characteristic of malignant tissue illustrates the application of this method.
REFERENCES:
patent: 4172124 (1979-10-01), Koprowski et al.
patent: 4471057 (1984-09-01), Koprowski et al.
patent: 4736022 (1988-04-01), Rademacher et al.
patent: 4752569 (1988-06-01), Terasaki et al.
patent: 4761401 (1988-08-01), Couchman et al.
patent: 4767845 (1988-08-01), Lemieux et al.
patent: 4774231 (1988-09-01), Petitou et al.
patent: 4794176 (1988-12-01), Lemieux et al.
patent: 4801583 (1989-01-01), Petitou et al.
patent: 4818816 (1989-04-01), Petitou et al.
patent: 4866041 (1989-09-01), Lemieux et al.
patent: 4904596 (1990-02-01), Hakomori
patent: 4980462 (1990-12-01), Karlsson et al.
patent: 5034516 (1991-07-01), Roy et al.
patent: 5059535 (1991-10-01), Mazid et al.
patent: 5075218 (1991-12-01), Jette et al.
patent: 5138044 (1992-08-01), Dasgupta
patent: 5296594 (1994-03-01), Ratcliffe et al.
patent: 5344870 (1994-09-01), Ratcliffe et al.
patent: 5352670 (1994-10-01), Venot et al.
Paulson et al., "Enzymatic Properties of B-D-Galactoside .alpha.2.fwdarw.6 Sialytransferase from Bovine Colostrum," J Biol Chem 252:2363-71 (1977).
Hakomori et al., "Human Cancor-Associated Gangliosides . . . ," Biochem Biophys Res Comm 113:791-98 (1983).
Achiba et al., "Preparation of Sialophosphorylglucosamine Derivatives as Immunostimulants," Chem. Abstracts, 108(19):694 abst. No. 167890a (1988).
Corifield et al., "Occurrence of Sialic Acids," Salic Acids, Chemistry, Metabolism and Function, pp. 5-50, Shauer, R. ed., Springer-Verlag, New York (1982).
Derappe et al., "Isolation and characterization of two sialyloligosaccharides containing N-acetyllactosamine from pregnancy urine," Carbohydrate Res., 145:341-347 (1986).
Feizi et al., "Carbohydrate structures of glycoproteins and glycolipids as differentiation antigens, tumour-associated antigens and components of receptor systems," TIBS, 24-29 (1985).
Fukuda et al., "Structure of Fetal Lactosaminoglycan," J. Biol. Chem., 259(8):4782-4791 (1984).
Fukushima et al., Chem Ab. 102(13):507 abst. No. 111029 k (1985).
Fukushima et al., "Characterization of Sialosylated Lewis.sup.X as a New Tumor-associated Antigen," Cancer Res. 44:5279-5285 (1984).
Hakomori, "Glycosphingolipids as differentiation-dependent, tumor-associated markers and as regulators of cell proliferation," TIBS, 453-459 (1984).
Hanisch et al., "Structure of Tumor-Associated Carbohydrate Antigen Ca 19-9 on Human Seminal Plasma Glycoproteins From Healthy Donors," Chem. Abstracts, 102(3):511-512 abst. No. 22471f (1985).
Hanish et al., Eur. J. Biochem., 144(3):467-473 (1984).
Hannson et al., "Biosynthesis of the Cancer-associated Sialyl-Le.sup.a Antigen," J. Biol. Chem., 260(16):9388-9392 (1985).
Holmes et al., "Biosynthesis of the Sailyl-Le.sup.x Determinant Carried by Type 2 Chain Glycosphingolipids (IV.sup.3 NeuAclll.sup.3 FucnLc.sub.4, Vl.sup.3 NeuAcV.sup.3 FucnLc.sub.6, and Vl.sup.3 NeuAclll.sup.3 V.sup.3 Fuc.sub.2 nLc.sub.6) in Human Lung Carcinoma PC9 Cells," J. Biol. Chem., 261:3737-3743 (1986).
Howard et al., "The GDP-fucose: N-Acetyl-glucosaminide 3-.alpha.L-Fucosytransferases of LEC11 and LEC12 Chinse Hamster Ovary Mutants Exhibit Novel Specificities for Glycolipid Substrates," J. Biol. Chem., 262:16,830-16,837 (1987).
Johnson et al., "Sialyl Compounds as Acceptor Substrates for Fucosyltransferases in Normal and Leukaemic Human Granulocytes," Biochem. Soc. Trans., 15:396 (1987).
Johnson et al., "Further Purification of the LeGene Associated m-L-Fucosyltransferase From Human Milk," Proc. IXth International Symposium of Glycoconjugates, Lille, France E107 (1987).
Johnson et al., "Acceptor Substrate Specificities for Glycolipid Substrates", Proc. Vlllth Int. Glycoconj. Symp., pp. 222-223 (1985).
Lamblin et al., "Primary Structure Determination of Five Sialyated Oligosaccharides Derived from Bronchial Mucus Glycoproteins of Patients Suffering from Cystic Fibrosis," J. Biol. Chem., 259(14):9051-9058 (1984).
Loomes et al., "Erythrocyte receptors for Mycoplasma pneumoniae are sialylated oligosaccharides of li antigen type," Nature, 307:560-563 (1984).
Magnani et al., "A Monoclonal Antibody-defined Antigen Associated with Gastrointestinal Cancer Is a Ganglioside Containing Sialylated Lacto-N-fucopentaose II," J. Biol. Chem., 257(23):14365-14369 (1982).
Numata et al., "Total Synthesis of Sialosylcerebroside, GM.sub.4," Carbohydrate Res., 163:209-225 (1987).
Ogawa et al., "Total Synthesis of a Undecasaccharide: A Typical Carbohydrate Sequence for the Complex Type of Glycan Chains of a Glycoprotein.sup.1," Tetrahedron Letters, 27(47):5739-5742 (1986).
Ogura et al., "Synthesis of 9-OACYL- And 4-(O-Acetyl-Sialic Acids," Carbohydrate Res., 167:77-86 (1987).
Parkkinen et al., "Isolation and Characterization of Novel Phosphate-Containing Sialyloligosaccharides From Normal Human Urine," Chem. Abstracts, 100(25):218 abst. No. 205293c (1984).
Paulsen et al., "Glycosidsynthese von N-Acetylneuraminsaure mit sekundaren Hydroxylgruppen," Carbo. Res. 146:147-153 (1986).
Paulsen et al., Chem. Abst., 105 Abst. No. 24548x (1986).
Paulsen et al., "Synthese Einer Disaccharideinheit Aus N-Acetylneuraminsaure Und 2-Acetamido-2-Desoxy-D-Galactose," Carboydrate Res., 137:63-77 (1985).
Paulsen et al., "Synthese Eines N-Acetylneuraminsaure-Haltigen Syntheseblocks. Kupplung Zum N-Acetylneuraminsaure-tetrasaccharid mit trimethylsilytriflat," Carbohydrate Res., 144:205-229 (1985).
Paulsen et al., "Synthese Eines Trisaccharides Aus N-Acetylneuraminsaure Und N-Acetyllactosamin," Carbohydrate Res., 125:47-64 (1984).
Paulson et al., "Selection of Influenza Virus Based on Sialyoligosaccharide Receptor Specificity," Pure & Appl. Chem., 56(7):797-805 (1984).
Pozgay et al., "A Novel Approach to N-Acetyl-Neuraminic Acid-Containing Oligosaccharides. Synthesis of a Glycosyl Donor Derivative of .alpha.-N-Acetyl-D-Neuraminyl-(2.fwdarw.6)-D-Galactos," J. Carboydrate Chem., 6(1):41-55 (1987).
Pozgay et al, "A Novel Approach to N-Acetylneuraminic acid-containing oligosaccharides," Chem. Abstracts, 108(19):abst. No. 167853r (1988).
Roy et al., "N-Acetylneuraminic Acid: Neoglycoproteins and Pseudopolysaccarides#," J. Carbohydrate Chem., 6(1):161-165 (1987).
Sabesan et al., "Combined Chemical and Enzymatic Synthesis of Sialyloligosaccharides and Characterization by 500-MHz .sup.1 H and .sup.13 C NMR Spectroscopy," J. Amer. Chem. Soc., 108:2068-2080 (1986).
Schauer, "Chemistry, Metabolism, and Biological Functions of Sialic Acids," Adv. Carbohydrate Chem. Biochem., 40:131-234 (1982).
Tamura et al., "Effect of complexation of silver ion with the glycosyl donor and acceptor on the regio- and stereo-selectivity in the .beta.-mannopyranosylation of 1,3-di-N-benzyloxycarbonyl-2-deoxystreptamine using silver triflate as a promoter in tetrahydrofuran," Carbohydrate Res., 207:153-165 (1990).
Abbas S. Zaheer
Ratcliffe Robert M.
Venot Andre P.
Alberta Research Council
Woodward Michael P.
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