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

Kubik, S.; Goddard, R.

doi:10.1073/pnas.062625299

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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

MPS-Authors

/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;

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

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: https://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.