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| Content Provider | World Health Organization (WHO)-Global Index Medicus |
|---|---|
| Author | Kubik, Stefan Goddard, Richard |
| Description | Author Affiliation: Kubik S ( Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität, Universitätsstrasse 1, D-40225 Düsseldorf, Germany. kubik@uni-duesseldorf.de); |
| Abstract | Two cyclic hexapeptides containing alternating all R and all S configured Ll-(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 hydroxyproline, 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% D(2)O/CD(3)OD. 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% D(2)O/CD(3)OD 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. |
| ISSN | 00278424 |
| e-ISSN | 10916490 |
| Journal | Proceedings of the National Academy of Sciences of the United States of America |
| Issue Number | 8 |
| Volume Number | 99 |
| Language | English |
| Publisher | National Academy of Sciences |
| Publisher Date | 2002-04-01 |
| Publisher Place | United States |
| Access Restriction | Open |
| Subject Keyword | Anions Hydroxyproline Chemistry Picolinic Acids Circular Dichroism Dimethyl Sulfoxide Kinetics Magnetic Resonance Spectroscopy Models, Chemical Models, Molecular Peptides Peptides, Cyclic Protein Conformation Research Support, Non-U.S. Gov't Multidisciplinary |
| Content Type | Text |
| Resource Type | Article |
| Subject | Multidisciplinary |
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