Highly selective lipophilic diboronic acid that transports fructose as the trisdentate 2,3,6-β-D-fructofuranose ester

被引：16

作者：

Draffin, SP

Duggan, PJ ^{[1
]}

Duggan, SAM

Norrild, JC

机构：

[1] Monash Univ, Sch Chem, Melbourne, Vic 3800, Australia

[2] Univ Copenhagen, Dept Chem, DK-2100 Copenhagen, Denmark

来源：

TETRAHEDRON | 2003年 / 59卷 / 46期

基金：

澳大利亚研究理事会;

关键词：

boronic acids; membrane transport; monosaccharides;

D O I：

10.1016/j.tet.2003.09.068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The transport of fructose and glucose through supported liquid membranes promoted by a tetrahedral shaped lipophilic monoboronic acid and diboronic acid, both based on a pentaerythritol core, has been studied. The diboronic acid gave a high fructose/glucose selectivity (7.7: 1.0). The results of molecular modelling studies and C-13 NMR experiments with uniformly labelled C-13-D-fructose suggest that the enhanced selectivity results from the formation of a trisdentate 2,3,6-beta-D-fructofuranose diester within the membrane. Experimental evidence for a previously proposed macrocyclic D-fructopyranose diester formed with an o-phenylene linked diboronic acid has also been found. (C) 2003 Elsevier Ltd. All rights reserved.

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收藏

页码：9075 / 9082

页数：8

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