Abstract: Processes are provided for the synthesis of the human T-antigenic determinant 2-acetamido-2-deoxy-3-O-(.beta.-D-galactopyranosyl)-.alpha.-D-galactopyran oside containing an .alpha.-O-glycosidically linked bridging arm O--(CH.sub.2).sub.n COR. The determinant is coupled to carrier molecules to form artificial T-antigens, and to insoluble supports to form T-immunoadsorbents. The artificial T-antigen is shown to elicit a delayed type hypersensitivity reaction as a diagnostic for the presence of cancer in humans.
Type:
Grant
Filed:
August 17, 1987
Date of Patent:
August 8, 1989
Assignee:
Chembiomed Ltd.
Inventors:
Raymond U. Lemieuz, Robert M. Ratcliffe, Donald A. Baker
Abstract: O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
Type:
Grant
Filed:
September 19, 1979
Date of Patent:
December 7, 1982
Assignee:
Chembiomed Ltd.
Inventors:
Raymond U. Lemieux, R. Murray Ratcliffe
Abstract: O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
Type:
Grant
Filed:
September 19, 1979
Date of Patent:
December 29, 1981
Assignee:
Chembiomed Ltd.
Inventors:
Raymond U. Lemieux, R. Murray Ratcliffe
Abstract: O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.
Type:
Grant
Filed:
April 7, 1978
Date of Patent:
March 25, 1980
Assignee:
Chembiomed Ltd.
Inventors:
Raymond U. Lemieux, R. Murray Ratcliffe