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

doi:10.1016/j.tet.2008.05.052

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

Research output: Contribution to journal › Article › Research › peer-review

18 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 language	English
Pages (from-to)	7122-7126
Number of pages	5
Journal	Tetrahedron
Volume	64
Issue number	30-31
DOIs	https://doi.org/10.1016/j.tet.2008.05.052
Publication status	Published - 21 Jul 2008
Externally published	Yes

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

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.",

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T1 - Enhanced fructose, glucose and lactose transport promoted by a lipophilic 2-(aminomethyl)-phenylboronic acid

AU - Duggan, Peter J.

AU - Houston, Todd A.

AU - Kiefel, Milton J.

AU - Levonis, Stephan M.

AU - Smith, Bradley D.

AU - Szydzik, Melanie L.

PY - 2008/7/21

Y1 - 2008/7/21

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AB - 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.

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

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