Multivalent ligands for the mannose-specific lectin on type 1 fimbriae of Escherichia coli:: syntheses and testing of trivalent α-D-mannoside clusters

被引:54
作者
Kötter, S
Krallmann-Wenzel, U
Ehlers, S
Lindhorst, TK
机构
[1] Univ Hamburg, Dept Organ Chem, D-20146 Hamburg, Germany
[2] Res Ctr, Div Mol Infect Biol, D-23845 Borstel, Germany
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 14期
关键词
D O I
10.1039/a801985a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The syntheses of the triantennary cluster alpha-D-mannosides 16, 19, 23 and 24 and their capacities to inhibit mannose-dependent binding of E, call HE 101 (pPK14) are described. The cluster glycosides are formed by glycosylation of tris-(3-hydroxypropyl)nitromethane 13, and by linking of suitable mannoside derivatives via amide and thiourea bonds to tris-(2-carboxyethyl)nitromethane 17 and tris-(2-aminoethyl)amine 20. Functionalized mannosides are attached to the core molecules at the 6-position of the sugar ring to allow variation of the introduced aglycone moieties in order to compare their effects on the inhibitory potencies of the derived mannoside clusters. The B-peptide-bridged cluster mannoside 19 displays the highest binding potency towards the type 1 fimbrial lectin of E. coli as tested by inhibition agglutination tests and ELISA.
引用
收藏
页码:2193 / 2200
页数:8
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