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Conformation and anion binding properties of cyclic hexapeptides containing L-4-hydroxyproline and 6-aminopicolinic acid subunits

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons58578

Goddard,  R.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Kubik, S., & Goddard, R. (2002). Conformation and anion binding properties of cyclic hexapeptides containing L-4-hydroxyproline and 6-aminopicolinic acid subunits. Proceedings of the National Academy of Sciences of the United States of America, 99(8), 5127-5132. doi:10.1073/pnas.062625299.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000F-99F5-6
Abstract
Two cyclic hexapeptides containing alternating all R and all S configured L-(4R/S)-hydroxyproline and 6-aminopicolinic acid subunits are presented, and the influence of the hydroxyl groups on the solubility, conformation, and receptor properties is investigated. Cyclopeptide 2, containing the natural 4R configured hydroxylproline, adopts a conformation similar to that of the unsubstituted peptide 1, which is able to bind anions such as halides and sulfate in aqueous solution. 2 also interacts with these anions, but whereas 1 forms sandwich type 2:1 complexes, in which the anion is bound by two cyclopeptide moieties, 2 forms 1:1 complexes. The stabilities of the halide and sulfate complexes of 2 range between 10(0) and 10(2) M-1 in 80% D2O/CD3OD. Complex formation is detectable even in water, but with slightly smaller stability constants. Using this information a quantitative evaluation of the stability of the 2:1 complexes of 1, for which overall stability constants in the order 10(4) to 10(5) M-2 in 80% D2O/CD3OD were observed, was made. In contrast to 2, the conformation of 3, containing the non-natural 4S configured hydroxyproline, is strongly affected by the presence of the hydroxyl groups. In d(6)-DMSO and methanol/water mixtures a slow conformational equilibrium between two C-3-symmetrical conformers is observed, and 3 is thus much less preorganized for anion binding than either 1 or 2.