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

Peter J. Duggan*, Todd A. Houston, Milton J. Kiefel, Stephan M. Levonis, Bradley D. Smith, Melanie L. Szydzik

*Corresponding author for this work

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17 Citations (Scopus)

Abstract

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 1a (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.

Original languageEnglish
Pages (from-to)7122-7126
Number of pages5
JournalTetrahedron
Volume64
Issue number30-31
DOIs
Publication statusPublished - 21 Jul 2008
Externally publishedYes

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