Synthesis of the breast tumor-associated antigen defined by mono

Details Synthesis of the breast tumor-associated antigen defined by mono Synthesis of the breast tumor-associated antigen defined by mono

1995-04-28

1998-01-13

Kight, John

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536 179, 536 552, 536 553, 536120, 5361231, 536126, C07H 100, C07H 506, C07H 1700, C08B 3700

Patent

active

057081638

ABSTRACT:
The present invention provides a process for synthesizing a compound having the structure: ##STR1## wherein R is H, as well as related oligosaccharides useful as a vaccine for inducing antibodies to human breast cancer cells in an adjuvant therapy therefor.

REFERENCES:
Behar, V. and S.J. Danishefsky, "A Highly Convergent Synthesis of the Lewis.sup.Y Blood Group Determinant in Conjugatable Form" Angewandte Chem. Int. Ed. Eng. (1994) 33(14): 1468-1470 (Exhibit 2).
Bremer, E.G., "Characterization of a Glycosphingolipid Antigen Defined by the Monoclonal Antibody MBrl Expressed in Normal and Neoplastic Epithelial Cells of Human Gland", J. Biol. Cham. (1984) 259: 14773-14777 (Exhibit 3).
Danishefsky, S.J., et al., "Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Le.sup.y and Le.sup.b Blood Group Determinants and H-Type I and H-Type II Oligosaccharides", J. Am. Chem. Soc. (1995) 117: 5701-5711 (Exhibit 4).
Dennis, J., Oxford Glycosystems Glyconews Second 1992 (Exhibit 5).
Feizi, T.,"Carbohydrate antigens in human cancer", Cancer Surveys (1985) 4: 245-269 (Exhibit 6).
Gorden, D.M. and Danishefsky, S.J., "Displacement reactions of a 1,2-anhydro-.alpha.-D-hexopyranose: installation of useful functionality at the anomeric carbon", Carbohydr. Res. (1990) 206: 361-366 (Exhibit 7).
Hakomori, S., "Aberrant Glycosylation in Cancer Cell Membranes as Focused on Glycolipids: Overview and Perspectives.sup.1 ", Cancer Res. (1985) 45: 2405-2414 (Exhibit 8).
Lay, L., et al., "Oligosaccharides Related to Tumor-Associated Antigens", Helv. Chim. Acta (1994) 77: 509-514 (Exhibit 9).
Lay, L., et al., "Oligosaccharides Related to Tumor-Associate Antigens", Helv. Chim. Acta (1995) 78: 533-538 (Exhibit 10).
Lloyd, K.O., "Blood Group Antigens as Markers for Normal Differentiation and Malignant Change in Human Tissues" Am. J. Clin. Pathol. (1987) 87: 129-139 (Exhibit 11).
Lloyd, K.O., "Humoral immune responses to tumor-associated carbohydrate antigens", Cancer Biol. (1991) 2: 421-431 (Exhibit 12).
Lloyd, K.O., In Specifice Immunotherapy of Cancer with Vaccines; New York Academy of Sciences; New York, 1993; vol. 690; pp. 50-58 (Exhibit 13).
Menard, S., et al., "Generation of Monoclonal Antibodies Reacting with Normal and Cancer Cells of Human Breast", Cancer Res. (1983) 43: 1295-1300 (Exhibit 14).
Randolph, J.T. and Danishefsky, S.J. "An Interactive Strategy for the Assembly of Complex Branched Oligosaccharide Domains Using Solid-Support Methods: An application to a Concise Synthesis of the Lewis.sup.b Domain in Bioconjugatable Form", Angewandte Chem. Int. Ed. Eng. (1994) 33(14): 1470-1473 (Exhibit 15).
Bernstein, M.A. and Hall, L.D., A General Synthesis of Model Glycoproteins: Coupling of Alkenyl Glycosides to Proteins, Using Reductive Ozonolysis Followed By Reductive Amination With Sodium Cyanoborohydride, Carbohydrate Research (1980) 78: C1-C3.
Danishefsky, S., et al., A Strategy For the Solid-Phase Synthesis of Oligosaccharides, Science (1993) 260: 1307-1309.
Gray, G.R., "Antibodies to Carbohydrates: Preparation of Antigens By Coupling Carbohydrates to Proteins By Reductive Amination With Cyanoborohydride", Methods in Enzymology (1978) 50: 155-160.
Mahajan, R., et al., "Synthesis of Neoglycoproteins as Artificial Antigens", J. Carbohydrate Chemistry (1994) 13(1): 63-73.

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