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1.
Bioorg Khim ; 20(5): 556-9, 1994 May.
Article in Russian | MEDLINE | ID: mdl-7519858

ABSTRACT

HSO3-3'Gal beta 1-3(Fuc alpha 1-4)GlcNAc beta 1-O(CH2)3NH2 was synthesized by selective sulfation (Py.SO3/Py, O degree C) of a protected trisaccharide Lea derivative bearing unsubstituted hydroxyls at C2 and C3 of the galactose moiety, BdGal beta 1-3(Bn3Fuc alpha 1-4)6-BnGlcNAc beta 1-O(CH2)3NHCOCF3, followed by convenient deprotection. A monosaccharide derivative, HSO3-3Gal beta 1-O(CH2)3NH2, was also obtained in a similar way. Coupling of the aminopropyl glycosides with poly(4-nitrophenylacrylate) gave rise to polyacrylamide (PAA) conjugates; biotinylated probes of the Sug-PAA-biotin type were obtained as well.


Subject(s)
Cell Adhesion Molecules/metabolism , Membrane Glycoproteins/chemistry , Oligosaccharides/chemical synthesis , Sulfuric Acids/chemistry , Carbohydrate Sequence , E-Selectin , Ligands , Membrane Glycoproteins/metabolism , Molecular Sequence Data , Oligosaccharides/metabolism
2.
Bioorg Khim ; 19(11): 1095-101, 1993 Nov.
Article in Russian | MEDLINE | ID: mdl-8285923

ABSTRACT

The determinant trisaccharide of the blood group A, GalNAc alpha 1-3(Fuc alpha 1-2)Gal beta, was modified by treatment of the trisaccharide acetate with phosphorus pentasulphide to convert its acetamide fragment determining the serological difference between antigenic determinants A and B into the thioacetamide derivative. Thionated analogues of the A disaccharide and of GalNAc alpha-glycoside were obtained in a similar way. Interaction of three monoclonal anti-A antibodies with modified antigens was studied using ELISA, the O-->S replacement allowing to evaluate the contribution of the acetamido carbonyl group into the antigen-antibody interaction.


Subject(s)
ABO Blood-Group System/chemistry , Thioacetamide/chemistry , Trisaccharides/chemistry , ABO Blood-Group System/immunology , Antibodies, Monoclonal/immunology , Antigen-Antibody Reactions , Carbohydrate Sequence , Enzyme-Linked Immunosorbent Assay , Humans , Molecular Sequence Data , Trisaccharides/immunology
3.
Bioorg Khim ; 17(9): 1177-87, 1991 Sep.
Article in Russian | MEDLINE | ID: mdl-1725479

ABSTRACT

Fine epitope specificity of ten monoclonal antibodies (MA) agglutinating red blood cells B was studied. Three methods were used: 1) inhibition of MA binding to natural antigen by synthetic oligosaccharides (OS) and their polyacrylamide conjugates, 2) direct MA binding to a series of synthetic OS-polyacrylamide conjugates differing in carbohydrate epitope density, 3) direct MA binding to the affinity sorbents. It is shown that all antibodies studied prefer trisaccharide B determinant Gal alpha 1-3(Fuc alpha 1-2) Gal independently of their ability to discriminate serological subgroups of B erythrocytes (B, Bweak, B3). The correlation of the MAs epitope specificity with their ability to agglutinate red blood cells B subgroups is discussed. Of an interest is that MAs which are able to agglutinate any B subgroups also bing the synthetic tetrasaccharide Gal alpha 1-3(Fuc alpha 1-2)Gal beta 1-3GalNAc, a B type 3 determinant.


Subject(s)
Antibodies, Monoclonal/immunology , Epitopes/immunology , Hemagglutination , ABO Blood-Group System/immunology , Erythrocytes/immunology , Fluorescent Antibody Technique , Humans , Membranes, Artificial , Oligosaccharides , Substrate Specificity
4.
Bioorg Khim ; 16(8): 1096-104, 1990 Aug.
Article in Russian | MEDLINE | ID: mdl-2285426

ABSTRACT

Chemical synthesis of A, B, and H (type 3) human blood group determinant oligosaccharides (as R-glycosides, R = OCH2CH2CH2NHCOCF3) and their polymeric derivatives are reported. 4,6; 4',6'-Di-O-benzylidene derivative of Gal beta 1----3GalNAc alpha 1----R was chloroacetylated selectively at 3'-OH, the chloroacetate was alpha-fucosylated and dechloroacetylated to give protected H (type 3) trisaccharide bearing free 3'-OH. alpha-Glycosylation of the trisaccharide with 2-azido-3,4,6-tri-O-benzyl-beta-D-galactopyranosyl chloride and 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl bromide gave rise to protected A and B tetrasaccharides, respectively. Deprotected R-glycosides were converted to OCH2CH2CH2NH2 derivatives. Their reaction with poly(4-nitrophenylacrylate) affords polyacrylamide-coupled conjugates with A, B, and H (type 3) specificity.


Subject(s)
ABO Blood-Group System/immunology , Oligosaccharides/chemical synthesis , Antibodies, Monoclonal/immunology , Carbohydrate Sequence , Humans , Molecular Sequence Data , Oligosaccharides/chemistry , Oligosaccharides/immunology , Sensitivity and Specificity
5.
Bioorg Khim ; 12(4): 533-8, 1986 Apr.
Article in Russian | MEDLINE | ID: mdl-3718549

ABSTRACT

Bioside Gal beta 1-3GalNAc alpha 1-O(CH2)3NHCOCF3 has been synthesized. The key alpha-glycoside GalNAc alpha 1-O(CH2)3NHCOCF3 (peracetate) was obtained either by isomerization of its beta-anomer with trifluoromethanesulfonic acid, or by direct glycosylation of 3-(trifluoroacetamido)propanol with D-galactosamine (anomeric pentaacetate) in the presence of a mixture of trifluoromethanesulfonic acid and boron trifluoride etherate. De-O-acetylated alpha-galactosaminide obtained was further transformed into benzylidene derivative, the latter was glycosylated with acetobromogalactose to give the protected alpha-bioside. The removal of the protecting groups gave the (3-aminopropyl)-alpha-bioside, which was subsequently immobilized on bovine serum albumin and cytochrome c.


Subject(s)
Antigens, Tumor-Associated, Carbohydrate , Disaccharides , Galactosamine/analogs & derivatives , Isoantigens , Animals , Chemical Phenomena , Chemistry , Galactosamine/chemical synthesis , Immunization , Isomerism
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