Enhanced fructose, glucose and lactose transport promoted by a lipophilic 2-(aminomethyl)-phenylboronic acid

被引：16

作者：

Duggan, Peter J. ^{[1
,2
]}

Houston, Todd A. ^{[3
]}

Kiefel, Milton J. ^{[3
]}

Levonis, Stephan M. ^{[3
]}

Smith, Bradley D. ^{[4
]}

Szydzik, Melanie L. ^{[2
]}

机构：

[1] CSIRO Mol & Hlth Technol, Clayton, Vic 3169, Australia

[2] Monash Univ, Sch Chem, Clayton, Vic 3800, Australia

[3] Griffith Univ, Inst Glyc, Nathan, Qld 4222, Australia

[4] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

TETRAHEDRON | 2008年 / 64卷 / 30-31期

关键词：

D O I：

10.1016/j.tet.2008.05.052

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A lipophilic 2-(aminomethyl)-phenylboronic acid (1a) was prepared and used to transport saccharides across a thin supported liquid membrane. The result was the highest recorded fructose flux promoted by a monoboronic acid under near-neutral conditions, and one of the highest fructose/glucose transport selectivities (12.9). The application of a pH gradient across the membrane further enhanced carrier-mediated fructose flux but fructose/glucose selectivity was decreased. The first effective transport of a disaccharide, lactose, was achieved using supported liquid membranes containing a high concentration of la (250 mM). A strong carrier concentration effect on lactose transport and a battery of mass spectrometry evidence point to the involvement of 2:1 boronate/lactose esters in this transport process. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：7122 / 7126

页数：5

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