We report that the amphiphilic 5 natural product,monoacylglycerol 1, functions as a transmembrane Cl-/NO3-anion transporter. The 1,2-diol group is crucial for transportfunction since diacylglycerol and triacylglycerol analogs arenot anion transporters. Furthermore, adding another10 hydrogen bond donor to the glycerol head-group andperfluorination of the acyl tail gave synthetic analogs withimproved Cl- membrane transport properties.We report that the amphiphilic natural product, monoacylglycerol, functions as a transmembrane Cl-/NO3- anion transporter. The 1,2-diol group is crucial for transport function since diacylglycerol and triacylglycerol analogs are not anion transporters. Furthermore, adding another hydrogen bond donor to the glycerol head-group and perfluorination of the acyl tail gave synthetic analogs with improved Cl- membrane transport properties. We demonstrate that adding hydrogen bond donor to the monoacylglycerol's head-group and increasing the lipophilicity of the acyl tail by perfluorination gave a synthetic analog that is almost 20-fold better at transporting chloride than the parent monoacylglycerol.

Monoacylglycerols as transmembrane chloride anion transporters

244th National Meeting (2012)

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