Synthesis of clustered D-GalNAc(Tn) and D-Gal beta(1->3)GalNAc(T) antigenic motifs using a pentaerythritol scaffold

被引:35
作者
Hanessian, S
Qiu, DX
Prabhanjan, H
Reddy, GV
Lou, BL
机构
[1] Department of Chemistry, Université de Montréal, Montréal, Que. H3C 3J7, Succ. Centre Ville
关键词
glycoside synthesis; 2-thiopyridyl carbonate; glycosyl donors and glycopeptide motifs;
D O I
10.1139/v96-192
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The tris(aminoethyl) and triamino derivatives of pentaerythritol have been used as scaffolds or templates for the attachment of immunologically relevant carbohydrates such as D-Gal beta(1 --> 3)GalNAc (T) and GalNAc (Tn), through amide linkages with the respective alpha-glycolyl and alpha-N-acetyl-L-serinyl glycosides. These clustered glycosidic motifs are intended as haptens for use in the preparation of tumor specific carbohydrate antigens and vaccines.
引用
收藏
页码:1738 / 1747
页数:10
相关论文
共 65 条
[1]  
ADACHI T, 1977, SYNTHESIS-STUTTGART, P45
[2]   MALIGNANT-CELL GLYCOPROTEINS AND GLYCOLIPIDS [J].
ALHADEFF, JA .
CRITICAL REVIEWS IN ONCOLOGY HEMATOLOGY, 1989, 9 (01) :37-107
[3]  
ARAWIND S, 1994, TETRAHEDRON LETT, V35, P7739
[4]  
BENCOMO VV, 1982, CARBOHYD RES, V110, pC9
[5]  
BYRSTRYN JC, 1990, CANCER METAST REV, V9, P81
[6]  
CIOMMER M, 1991, SYNLETT, P593
[7]  
DESAI P R, 1987, Journal of Tumor Marker Oncology, V2, P233
[8]  
DOHI T, 1988, CANCER RES, V48, P5680
[9]   SYNTHESIS OF DERIVATIVES OF 3-O-(2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSYL)-L-SERINE AND L-THREONINE [J].
FERRARI, B ;
PAVIA, AA .
CARBOHYDRATE RESEARCH, 1980, 79 (01) :C1-C7
[10]   SYNTHESIS OF 2-ACETAMIDO-2-DEOXY-3-O-(BETA-D-GALACTOPYRANOSYL)-ALPHA-D-GALACTOSE [J].
FLOWERS, HM ;
SHAPIRO, D .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (06) :2041-&