A highly practical synthesis of cyclodextrin-based glycoclusters having enhanced affinity with lectins

被引：67

作者：

Furuike, T

Aiba, S

Nishimura, SI ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Sci, Japan Bioind Assoc, Lab Glycocluster Project, Sapporo, Hokkaido 0600810, Japan

[2] AIST, Osaka Natl Res Inst, Dept Organ Mat, Ikeda, Osaka 5638577, Japan

[3] Hokkaido Univ, Grad Sch Sci, Div Biol Sci, Lab Bio Macromol Chem, Sapporo, Hokkaido 0600810, Japan

来源：

TETRAHEDRON | 2000年 / 56卷 / 51期

关键词：

cluster effect; glycocluster; cyclodextrin; glycocyclodextrin (glycoCD); wheat germ agglutinin WGA); Erythrina corallodendron lectin (ECorL);

D O I：

10.1016/S0040-4020(00)00962-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple and highly practical method for the synthesis of cyclodextrin-scaffolded glycoclusters recognized specifically by lectins is described. Nucleophilic displacement of iodide from heptakis 6-deoxy-6-iodo-beta -cyclodextrin by unprotected sodium thiolates derived from 3-(3-thioacetyl propionamido)propyl glycosides proceeded smoothly in mild condition and gave novel per-glycosylated cyclodextrins (glycocyclodextrins, glycoCDs) having D-galactose, N-acetyl-D-glucosamine, lactose or N-acetyllactosamine residues in high yields (78-88%). It was demonstrated that all these per-glycosylated P-cyclodextrins showed amplified inhibitory effects on the erythrocytes agglutination induced by wheat germ (Triticum vulgaris) agglutinin (WGA) or Erythrina corallodendron lectin (ECorL). (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：9909 / 9915

页数：7

共 56 条

[1] Globular carbohydrate macromolecule ''sugar balls'' .3. ''Radial-growth polymerization'' of sugar-substituted alpha-amino acid N-carboxyanhydrides (GlycoNCAs) with a dendritic initiator [J].