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

Scott P. Draffin; Peter J. Duggan; Sandhya A.M. Duggan

doi:10.1021/ol015560x

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

Scott P. Draffin, Peter J. Duggan, Sandhya A.M. Duggan

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

56 Citations (Scopus)

Abstract

matrix presented 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.

Original language	English
Pages (from-to)	917-920
Number of pages	4
Journal	Organic Letters
Volume	3
Issue number	6
DOIs	https://doi.org/10.1021/ol015560x
Publication status	Published - 22 Mar 2001
Externally published	Yes

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N2 - matrix presented 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.

AB - matrix presented 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.

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

Abstract

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