Carbamate triserine lactone receptors for anion recognition

• Published in: Tetrahedron letters Vol. 49; no. 45; pp. 6410 - 6412
• Main Authors: Wang, Yizhe, Duran, Edward, Nacionales, David, Valencia, Amber, Wostenberg, Christopher, Marinez, Eric R.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 03-11-2008
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2008.08.081

We have taken advantage of the ability of the cyclic triester of
l-serine to organize ligand units appended to the three α-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.