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

Research output: Contribution to journalArticleResearchpeer-review

16 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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Lactose
Fructose
Glucose
Liquid membranes
Membranes
Fluxes
Proton-Motive Force
Disaccharides
Carrier concentration
Mass spectrometry
Mass Spectrometry
Esters
Acids
benzeneboronic acid

Cite this

Duggan, Peter J. ; Houston, Todd A. ; Kiefel, Milton J. ; Levonis, Stephan M. ; Smith, Bradley D. ; Szydzik, Melanie L. / Enhanced fructose, glucose and lactose transport promoted by a lipophilic 2-(aminomethyl)-phenylboronic acid. In: Tetrahedron. 2008 ; Vol. 64, No. 30-31. pp. 7122-7126.
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Enhanced fructose, glucose and lactose transport promoted by a lipophilic 2-(aminomethyl)-phenylboronic acid. / Duggan, Peter J.; Houston, Todd A.; Kiefel, Milton J.; Levonis, Stephan M.; Smith, Bradley D.; Szydzik, Melanie L.

In: Tetrahedron, Vol. 64, No. 30-31, 21.07.2008, p. 7122-7126.

Research output: Contribution to journalArticleResearchpeer-review

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