Highly Fructose Selective Transport Promoted by Boronic Acids Based on a Pentaerythritol Core

Highly Fructose Selective Transport Promoted by Boronic Acids Based on a Pentaerythritol Core

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...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2001-03, Vol.3 (6), p.917-920
Hauptverfasser: Draffin, Scott P, Duggan, Peter J, Duggan, Sandhya A. M
Format: Artikel
Sprache:eng
Schlagworte:
Boronic Acids - chemical synthesis
Boronic Acids - chemistry
Carbohydrate Conformation
Esters
Fructose - chemistry
Indicators and Reagents
Models, Molecular
Molecular Conformation
Molecular Structure
Propylene Glycols - chemistry
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
Beschreibung
Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol015560x