Abrasive tool making process – material – or composition
Patent
1994-10-20
1999-02-16
Peselev, Elli
Abrasive tool making process, material, or composition
514 23, 514 25, 514 60, 530322, 536 111, 536 172, 536 179, 536 187, 536 221, A61K 3816, A61K 3170, C07K 900, C07M 1500
Patent
active
058720960
ABSTRACT:
The present invention is drawn to methods for the synthesis of Lewis.sup.a derivatives modified at the C-2 and/or C-6 position of GlcNAc employing chemo-enzymatic synthesis. The derivatives find use in the treatment and prevention of diseases.
REFERENCES:
patent: 4612132 (1986-09-01), Wollenberg et al.
patent: 4727136 (1988-02-01), Jennings et al.
patent: 5079353 (1992-01-01), Ratcliffe et al.
patent: 5344870 (1994-09-01), Ratcliffe et al.
patent: 5352670 (1994-10-01), Venot et al.
patent: 5374655 (1994-12-01), Kashem et al.
Ichikawa, Y., et al., "Chemical-Enzymatic Synthesis and Conformational Analysis of Sialyl Lewis x and Derivatives" Am. Chem. Soc. 114:9283-9298 (1992).
Watkins, W., et al., "Human Fucosyltransferases" Am. Chem. Soc., Ch. 4, pp. 34-61 (1993).
Baba, et al., "Suppression of Cell-Mediated Immune Reactions by Monosaccharides", J. Immunology, vol., 122, No. 3, pp. 838-841 (1979).
Hilgert, et al., "Lentil Lectin Effectively Induces Allotransplantation Tolerance in Mice", Nature, 284:273-275 (1980).
Spohr, et al., "Synthetic, Conformational, and Immunochemical Studies of Modified Lewis b and Y Human Blood-Group Determinants to Serve as Probes for the Combining Site of the Lectin IV of Griffonia simplicifolia", Carbohydrate Res., 174:211-237 (1988).
Springer, et al., "Sticky Sugars for Selectins", Nature, 349:196-197 (1991).
Barsoum and Davidson, Mol. Immunol., 18:367-372 (1981).
Beyer et al., J. Biol. Chem., 254:12531-12541 (1979).
Conradt et al., Japanese-German Symp. Berlin, 104-105 (1988).
Dumas et al., Bioorg. Med. Chem. Letters, 1:425-428 (1991).
Eppenberger-Castori et al., Glycoconj. J. 6:101-114 (1989).
Fung et al., Cancer Res., 50:4308-4314 (1990).
Hakomori, Adv. Cancer Res., 52:257-331 (1989).
Handa and Nakamuram J. Biochem., 95:1323-1329 (1984).
Henningsson et al., Cancer Immunol. Immunother., 25:231-241 (1987).
Houghton et al., Symposium on Gangliosides and Cancer, pp. 232-237, VCH Publishers (1988).
Howard, in "Towards Better Carbohydrate Vaccines"; Proceedings of a Meeting Organized by the World Health Organization, R. Bell, G. Torrigani, Editors, pp. 221-231, Wiley, Chichester (1987).
Ichikawa et al., Anal. Bio. Chem., 202:215-238.
Irie et al., Symposium on Gangliosides and Cancer, pp. 247-257, VCH Publishers (1988).
Johnson and Watkins, VIIIth Int. Symp. Glycoconjugates, Houston, 2:222-223 (1985).
Kukowska-Latallo et al., Genes & Development, 4:1288-1303 (1990).
Livingston et al., Proc. Natl. Acad. Sci. USA, 84:2911-2915 (1987).
Nakamura and Handa, J. Biochem., (Tokyo) 99:219-226 (1986).
Naor and Galili, Prog. Allergy, 22:107-146 (1977).
Orskov et al., J. Exp. Med., 149:669-685 (1979).
Palcic et al., Carbohydr. Res., 190:1-11 (1989).
Paulson et al., Eur. J. Biochem., 140:523-530 (1984).
Prieels et al., J. Biol. Chem., 256:10456-10463 (1981).
Rearick et al., J. Biol. Chem., 254:4444-4451 (1979).
Ritter, Immunobiology, 182:32-43 (1991).
Sabesan and Paulson, J. Am. Chem. Soc., 108:2068-2080 (1986).
Weinstein et al., J. Biol. Chem., 257:13835-13844 (1982).
Weinstein et al., J. Biol. Chem., 257:13845-13853 (1982).
Baba, et al., J. Immuno., 122(3):838-841 (1979).
Watanabe, Jpn. J. Cancer Res., 76:43-52 (1985).
Phillips, Science, 250:1130-1132 (1990).
Walz, et al., Science, 250:1132-1135 (1990).
Amvam-Zollo, P., et al. "Streptococcus pneumoniae Type XIVPolysaccharide: Synthesis of a Repeating Branched Tetrasaccharide with Dioxa-Type Spacer-Arms", Carbohydrate Research, 150:199-212 (1986).
Aplin, J. D., et al. "Preparation, Properties, and Applications ofCarbohydrate Conjugates of Proteins and Lipids," CRC Critical Reviews in Biochemistry, 259-306 (1981).
Barsoum et al., Mol. Immunol., 18:495-550 (1981).
Belkhouya, N., et al. "Halogenation Selective en C-6 de 2-Amino-2-Desoxy-D-Glycopyranoses," 3977-3980 (1991).
Bernotas, R.C., et al. "Easy assembly for ligands for glycosidase affinity chromatography," Biochem. J., 270:539-540 (1990).
Bernstein, M.A., et al. "A general synthesis of model glycoproteins: coupling of alkenyl glycosides to proteins, using reductive ozonolysis followed by reductive amination with sodium cyanoborohydride," Carbohydrate Research, 78:C1-C3 (1980).
Bradford, M.M. "A Rapid and Sensitive Method for the Quantitiation of Microgram Quantities of Protein Utilizing the Principle of Protein-Dye Binding," Analytical Biochemistry, 72:248-254 (1976).
Brandley, B.K., et al. "Carbohydrate Ligands of the LEC Cell Adhesion Molecules," Cell, 63:861-863 (1990).
Brossmer, R., et al. "Enzymic Synthesis of 5-Acetamido-9-Azido-3, 5, 9-Trideoxy-D-glycero-D-galacto-2-Nonulosonic Acid, A 9-Azido-9-Deoxy Derivative of N-Acetylneuraminic Acid," Biochem. and Biophys. Res. Comm., 96:3, 1282-1289 (1980).
Chernyak, A. Y., et al. "A New Type of Carbohydrate-Containing Synthetic Antigen: Synthesis of Carbohydrate-Containing Polyacrylamide Copolymers having the Specificity of 0:3 and 0:4 Factors of Salmonella," Carbohydrate Research, 128:269-282 (1984).
Christian, R., et al. "On the Side-Chain Conformation of N Acetylneuraminic Acid and its Epimers at C-7, C-8, and C-7,8,"Christian et al., Carbohydr. Res., 162:1-11 (1987).
Christian, R. "The Side-Chain Conformations of N-Acetyl-7, 8-, 9-Deoxy-, and 4.7-Dideoxy-Neuraminic Acid and Their Effects on The Activation of CIP:N-Acylneuramininc Acid Cytidylyl-Transferase," Carbohy. Res., 194;49-61 (1989).
Conradt, H.S., et al. "Preparation of (1984).
Dahmen, J., et al. "2-Bromoethyl glycosides: applications in the synthesis of spacer-arm glycosides," Carbohydrate Research, 118:292-301 (1983).
Dean, P.D.G., et al. "Protein Purification using Immobilised Triazine Dyes," Journal of Chromatography, 165:301-319 (1979).
Dick, W.E., et al. "Glycoconjugates of Bacterial Carbohydrate Antigens," Contributions to Microbiology and Immunology, 10:48-114 (1989).
Ekborg, G., et al. "Synthesis of Three Disaccharides for the Preparation of Immunogens bearing Immunodeterminants Known to Occur on Glycoproteins," Carbohydrate Research, 110:55-67 (1982).
Feizi, TIBS, 16:84-86 (1991).
Fernandez, V., et al. "Glycosides of Monoallyl Diethylene Glycol. A New type of Spacer group for Synthetic Oligosaccharides," J. Carbohydrate Chemistry, 8(3), 531-537 (1989).
Gokhale, U.B., et al. "Chemical synthesis of GDP-fucose analogs and their utilization by the Lewis a(1.fwdarw.4) fucosyltransferase," Can. J. Chem., 68: 1063-1071 (1990).
Greig, C.G., et al. "The Preparation of Phenyl 2-Amino-2-deoxy-.beta.-D-glucopyranoside and Some 2-Acylamino-derivatives thereof," 879-883 (1961).
Gross, H. J. et al. "N-Acetyl-4-deoxy-D-neuraminic Acid is Activated and Transferred on to Asialoglycoprotein," Glycoconjugate, 4:145-156 (1987).
Gross, H.J., et al. "Activation and Transfer of Novel Synthetic 9 Substituted Sialic Acids," Eur. J. Biochem., 168: 595-602 (1987).
Gross, H.J., et al. "Enzymatic Introduction of a Fluorescent Sialic Acid into Oligosaccharide Chains of Glycoproteins," Eur. J. Biochem., 177: 583-589 (1988).
Handa, S. et al. "Modification of Sialic Acid Carboxyl Group of Ganglioside," J. Biochem., 95: 1323-1329 (1984).
Hagedorn et al., "6-Thio Sialic Acid And 4-Deoxy Sialic Acid" XIIIth Carbohydr. Symp., Ithaca (1986)A4.
Hannesian, "The Reaction of O-benzylideno sugars with N-bromosuccinimide", 2:86-88 (1966).
Haverkamp, et al. "Improved Synthesis of CMP-Sialates Using Enzymes from Frong Liver and Equine Submandibular Gland," Hoppe-Seyler's Z. Physiol. Chem., 360: 159-166 (1979).
Higa, H. H. "Sialylation of Glycoprotein Oligosaccharides with N-Acetyl-, N-Glycolyl-, and N-O-Diacetylneuraminic Acids," J. of Biol. Chem., 260: 8838-8849 (1985).
Horowitz, The Glycoconjugates, vols. I-V, Pigman, Ed., New York, Academic Press (1977, 1978, 1982, 1983).
Inazu, T., et al. "New Synthetic Methods and Reagents for Complex Carbohydrates. II. Synthesis of 2-Acylamino-2-deoxy-D-glucopyranose Derivatives by Dimethylphosphinothioic Mixed Anhydride Method," Bull. Chem. Soc. Jpn., 611: 4467-4469 (1988).
Kovac, P., et al. "Synthesis and N.M.R. Spectra of Methyl 2-Deoxy-2-Fluoro-and 3-Deoxy-3-Fluoro-.alpha.- and .beta.-D-Glucopyranosides," Carbohydrate Research, 169:23-34 (1987
Kashem Mohammed A.
Nikrad Pandurang V.
Venot Andre P.
Alberta Research Council
Peselev Elli
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