Highly fructose selective transport promoted by boronic acids based on a pentaerythritol core

被引：51

作者：

Draffin, SP ^{[1
]}

Duggan, PJ ^{[1
]}

Duggan, SAM ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 06期

关键词：

D O I：

10.1021/ol015560x

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We have designed and synthesized a highly lipophilic boronic acid (11) with a molecular shape that makes it much more effective at carrying sugars through organic membranes than a previously used steroidal boronic acid. The corresponding diboronic acid (12) was also found to transport fructose ahead of glucose with a very high selectivity (7.6:1.0). Modeling suggests that 12 is able to carry two fructose molecules at once in a complex stabilized through hydrogen bonding and ion pairing.

引用

页码：917 / 920

页数：4

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