Synthesis of neoglycoproteins containing O-methylated trisaccharides related to excretory/secretory antigens of Toxocara larvae

被引:17
作者
Amer, H [1 ]
Hofinger, A [1 ]
Kosma, P [1 ]
机构
[1] Univ Agr Sci, Inst Chem, A-1190 Vienna, Austria
关键词
neoglycoprotein; Toxocara; antigen; O-glycan; fucose;
D O I
10.1016/S0008-6215(02)00355-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The disaccharides allyl beta-D-galactopyranosyl-(1 --> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 10a and 10b and the trisaccharides allyl 2-O-methyl-alpha-L-fucopyranosyl-(1 --> 2)-beta-D-galactopyranosyl-(1--> 3)-2-acetamido-2-deoxy-beta- and alpha-D-galactopyranoside 18a and 18b have been prepared using stepwise assembly of the sugar units. The glycosidic linkages were formed employing the trichloroacetimidate procedure for the attachment of the galactopyranosyl residue and N-iodosuccinimide/triflic acid activation of an ethyl 1-thiofucopyranoside donor for fucosylation. Deprotection furnished the allyl glycosides which were converted into cysteamine-spacered ligands, activated with thiophosgene and subsequently linked to bovine serum albumin. The neoglycoproteins serve as immunoreagents to determine epitope specificities of monoclonal antibodies directed against highly immunogenic O-glycans located at the surface of Toxocara larvae. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:35 / 45
页数:11
相关论文
共 31 条
[1]   Synthesis of O-methylated disaccharides related to excretory/secretory antigens of Toxocara larvae [J].
Amer, H ;
Hofinger, A ;
Puchberger, M ;
Kosma, P .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2001, 20 (7-8) :719-731
[2]  
Burkhart F, 2001, ANGEW CHEM INT EDIT, V40, P1274, DOI 10.1002/1521-3773(20010401)40:7<1274::AID-ANIE1274>3.0.CO
[3]  
2-W
[4]   EFFICIENT SYNTHESES OF METHYL 2-3-BENZOYL-4,6-0-BENZYLIDENE-ALPHA-GLUCOPYRANOSIDE AND METHYL 2-0-BENZOYL-4,6-0-BENZYLIDENE-ALPHA-D-RIBO-HEXOPYRANOSID-3-ULOSE [J].
CAREY, FA ;
HODGSON, KO .
CARBOHYDRATE RESEARCH, 1970, 12 (03) :463-&
[5]   CHEMICAL SYNTHESIS OF THE DESIALYLATED HUMAN CAD-ANTIGENIC DETERMINANT [J].
CATELANI, G ;
MARRA, A ;
PAQUET, F ;
SINAY, P .
CARBOHYDRATE RESEARCH, 1986, 155 :131-140
[6]   MOLECULAR RECOGNITION .12. THE BINDING OF THE H-HUMAN BLOOD-GROUP DETERMINANTS AND CONGENERS BY A LECTIN OF GALACTIA-TENUIFLORA [J].
CROMER, R ;
SPOHR, U ;
KHARE, DP ;
LEPENDU, J ;
LEMIEUX, RU .
CANADIAN JOURNAL OF CHEMISTRY, 1992, 70 (05) :1511-1530
[7]   An abundantly expressed mucin-like protein from Toxocara canis infective larvae: The precursor of the larval surface coat glycoproteins [J].
Gems, D ;
Maizels, RM .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (04) :1665-1670
[8]  
KHOO K-H, 1991, Glycobiology, V1, P163, DOI 10.1093/glycob/1.2.163
[9]   FERRIC CHLORIDE-CATALYZED GLYCOSYLATION OF ALCOHOLS BY 2-ACYLAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE 1-ACETATES [J].
KISO, M ;
ANDERSON, L .
CARBOHYDRATE RESEARCH, 1979, 72 (JUL) :C12-C14
[10]  
Lassaletta JM, 1996, LIEBIGS ANN, P1417