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 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.
Draffin
S P
SP
Centre for Green Chemistry, School of Chemistry, P.O. Box 23, Monash University, Clayton, Melbourne, Victoria 3800, Australia.
Duggan
P J
PJ
Duggan
S A
SA
D001897:Boronic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D004952:Esters; D005632:Fructose / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D011409:Propylene Glycols / Q000737:chemistry*
D001897:Boronic Acids; D004952:Esters; D007202:Indicators and Reagents; D011409:Propylene Glycols; D005632:Fructose; C008783:pentaerythritol