Carbamate triserine lactone receptors for anion recognition

We have taken advantage of the ability of the cyclic triester of L-serine to organize ligand units appended to the three alpha-amine functionalities, as in enterobactin, a siderophore produced by enteric bacteria that binds ferric ion exceptionally well (K-f = 10(49)). As an extension of the preorganization concept, this work describes the preparation and characterization of carbamate triserine lactone receptors 1-6 and their ability to act as molecular receptors for anions. These receptors bind halides (F- >> Cl- > Br- > I-) with binding constants K in the range 21-7350 L mol(-1). (C) 2008 Elsevier Ltd. All rights reserved.