Title:
PROCESS FOR PREPARATION OF GLYCOSIDES OF TUMOR-ASSOCIATED CARBOHYDRATE ANTIGENS
Document Type and Number:
WIPO Patent Application WO1995029927
Kind Code:
A3
Abstract:
Glycoconjugate antigens are prepared by preparing a hapten glycoside, especially an alpha glycoside prepared by the Fischer method, with an olefinic aglycon moiety, especially one having a non-terminal double bond, ozonolyzing the hapten glycoside with an olefinic aglycon moiety having a non-terminal double bond to form a hapten-glycoside derivative, preferably without producing Germaldehyde as a byproduct removing by-products of ozonolysis, and conjugating the hapten-glycoside derivative to a carrier.
Inventors:
WONG TING CHI
KOGANTY R RAO
KOGANTY R RAO
Application Number:
PCT/IB1995/000363
Publication Date:
June 06, 1996
Filing Date:
April 28, 1995
Export Citation:
Assignee:
BIOMIRA INC (CA)
MCINNIS PATRICIA (CA)
MCINNIS PATRICIA (CA)
International Classes:
C07H3/06; C07H9/06; C07H15/04; C07H15/10; (IPC1-7): C07H15/10
Foreign References:
| US4935503A | 1990-06-19 | |||
| US4563445A | 1986-01-07 |
Other References:
J. DIAKUR AND A.A. NOUJAIM: "Synthesis of GD3 as a 4-methyl-3-pentenyl glycoside and subsequent conjugation to HSA", J. CARBOHYDR. CHEM., vol. 13, no. 5, pages 777 - 797
M.A. BERNSTEIN ET AL.: "A general synthesis of model glycoproteins: coupling of alkenyl glycosides to proteins, using reductive ozonolysis followed by reductive amination with sodium cyanoborohydride", CARBOHYDR. RES., vol. 78, pages C1 - C3
R.T. LEE AND Y.C. LEE: "Synthesis of 3-(2-aminoethylthio)propyl glycosides", CARBOHYDR. RES., vol. 37, pages 193 - 201
S. HANESSIAN ET AL.: "Conformational analysis of the carbohydrate portion of T and Tn haptens by nmr spectroscopy and molecular modeling", TETRAHEDRON, vol. 50, pages 77 - 92
D. CABARET ET AL.: "Amphiphilic liposaccarides. Synthesis and reductive cleavage of C-allyl, O-allyl, and O-butenyl glycosyl derivatives", CARBOHYDR. RES., vol. 189, pages 341 - 348
G.O. ASPINALL ET AL.: "Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens", CARBOHYDR. RES., vol. 216, pages 337 - 355
G.O. ASPINALL ET AL.: "A stereoselective synthesis of pyruvic 4,6-acetals of D-hexopyranose residues", CARBOHYDR. RES., vol. 200, pages 247 - 256
K.R. HOLME ET AL.: "Preparation and characterization of N-(2-(glycosyloxy)ethyl)chitosan derivatives", CARBOHYDR. RES., vol. 225, pages 291 - 306
HOUBEN-WEYL: "Methoden der Organischen Chemie, Band VII, Teil 1", E. MÜLLER, STUTTGART
T.C. WONG ET AL.: "Synthesis of D-Galactosamine Derivatives and Binding Studies Using Isolated Rat Hepatocytes", CARBOHYDR. RES., vol. 170, pages 27 - 46
R.W JEANLOZ ET AL.: "The Synthesis of Allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside and of Chitobiose Derivatives by the Oxazoline Procedure", CARBOHYDR. RES., vol. 53, pages 67 - 84
R. GIGG ET AL.: "Synthesis of Propyl 4-O-(3,6-di-O-methyl-beta-D-gluco- pyranosyl)-2,3-di-O-methyl-alpha-D-rhamno-pyranoside", CARBOHYDR. RES., vol. 141, pages 91 - 7
H.A. EL-SHENAWY ET AL.: "Studies on the Synthesis of Propyl 4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside", CARBOHYDR. RES., vol. 131, pages 227 - 38
M.A. BERNSTEIN ET AL.: "A general synthesis of model glycoproteins: coupling of alkenyl glycosides to proteins, using reductive ozonolysis followed by reductive amination with sodium cyanoborohydride", CARBOHYDR. RES., vol. 78, pages C1 - C3
R.T. LEE AND Y.C. LEE: "Synthesis of 3-(2-aminoethylthio)propyl glycosides", CARBOHYDR. RES., vol. 37, pages 193 - 201
S. HANESSIAN ET AL.: "Conformational analysis of the carbohydrate portion of T and Tn haptens by nmr spectroscopy and molecular modeling", TETRAHEDRON, vol. 50, pages 77 - 92
D. CABARET ET AL.: "Amphiphilic liposaccarides. Synthesis and reductive cleavage of C-allyl, O-allyl, and O-butenyl glycosyl derivatives", CARBOHYDR. RES., vol. 189, pages 341 - 348
G.O. ASPINALL ET AL.: "Synthesis of allyl glycosides for conversion into neoglycoproteins bearing epitopes of mycobacterial glycolipid antigens", CARBOHYDR. RES., vol. 216, pages 337 - 355
G.O. ASPINALL ET AL.: "A stereoselective synthesis of pyruvic 4,6-acetals of D-hexopyranose residues", CARBOHYDR. RES., vol. 200, pages 247 - 256
K.R. HOLME ET AL.: "Preparation and characterization of N-(2-(glycosyloxy)ethyl)chitosan derivatives", CARBOHYDR. RES., vol. 225, pages 291 - 306
HOUBEN-WEYL: "Methoden der Organischen Chemie, Band VII, Teil 1", E. MÜLLER, STUTTGART
T.C. WONG ET AL.: "Synthesis of D-Galactosamine Derivatives and Binding Studies Using Isolated Rat Hepatocytes", CARBOHYDR. RES., vol. 170, pages 27 - 46
R.W JEANLOZ ET AL.: "The Synthesis of Allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside and of Chitobiose Derivatives by the Oxazoline Procedure", CARBOHYDR. RES., vol. 53, pages 67 - 84
R. GIGG ET AL.: "Synthesis of Propyl 4-O-(3,6-di-O-methyl-beta-D-gluco- pyranosyl)-2,3-di-O-methyl-alpha-D-rhamno-pyranoside", CARBOHYDR. RES., vol. 141, pages 91 - 7
H.A. EL-SHENAWY ET AL.: "Studies on the Synthesis of Propyl 4-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside", CARBOHYDR. RES., vol. 131, pages 227 - 38
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