Design of Pseudodiproline Dimers as Mimetics of Pro-Pro Units: Stereocontrolled Synthesis, Configurational Relevance, and Structural Properties
| Autor: | Stephen Hanessian, Jean-Baptiste Garsi, Pedro Aguiar |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
chemistry.chemical_classification
0303 health sciences Enzyme complex Magnetic Resonance Spectroscopy Proline Peptidomimetic Stereochemistry Carboxylic acid Organic Chemistry Dipeptides 010402 general chemistry 01 natural sciences Pyrrolidine 0104 chemical sciences Amino acid 03 medical and health sciences Residue (chemistry) chemistry.chemical_compound chemistry Tetrahedral carbonyl addition compound Molecule Peptidomimetics 030304 developmental biology |
| Zdroj: | The Journal of organic chemistry. 86(23) |
| ISSN: | 1520-6904 |
| Popis: | Stereocontrolled methods are described for the synthesis of hitherto unreported pseudodiproline dimers in which a cyclopentane carboxylic acid is linked to a pyrrolidine residue by a stereochemically defined hydroxymethylene tether. These proline-cyclopentane (Pro-Cyp) dimers have interesting structural characteristics as seen in their X-ray crystal structures as well as their nuclear magnetic resonance (NMR) spectra in CDCl3. They can be considered to be novel Pro-Pro mimetics, which can be used to replace natural diproline sequences with potential applications in medicinal chemistry. They also represent a new concept in the peptidomimetic design of chimeric proline-based amino acids as carbocyclic hydroxyethylene isosteres of inhibitor molecules, in which the stereodefined bridging hydroxyl group can simulate a tetrahedral intermediate in an enzyme complex. |
| Databáze: | OpenAIRE |
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