PMID: 12467396Dec 7, 2002

Dual binding mode of methylmethanetriacetic Acid to tripodal amidopyridine receptors

The Journal of Organic Chemistry
P BallesterG Deslongchamps

Abstract

A series of tripodal amidopyridine receptors capable of selective recognition of methylmethanetriacetic acid (MMTA) in organic solvents is described. Intramolecular hydrogen-bonding groups, built into some of the receptors, were designed as preorganization devices. Binding was studied by NMR titration, variable temperature NMR experiments, 2D-NMR, isothermal titration calorimetry, and single-crystal X-ray crystallography. The results reveal that a balancing act between inter- and intramolecular hydrogen-bonding interactions in the complexes governs both the dynamics and the geometry of binding. Receptor 1b (without intramolecular hydrogen-bonding groups) features a simple symmetric MMTA binding geometry with optimal enthalpic interactions. In sharp contrast, receptor 1a (with intramolecular hydrogen-bonding groups) reveals a temperature-dependent dual binding mode where MMTA can bind in two completely different geometries. The two solution binding geometries of 1a.MMTA were unraveled by NMR experiments and correlated to the X-ray structures.

Citations

Jun 9, 2004·Current Opinion in Chemical Biology·Natarajan Srinivasan, Jeremy D Kilburn
Sep 24, 2004·Journal of Molecular Recognition : JMR·Matthew J CliffJohn E Ladbury
Oct 26, 2010·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ruud CuypersHan Zuilhof
Jan 19, 2006·Critical Reviews in Microbiology·Gonzalo R TortellaNelson Duran

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