Synthesis of a val-pro diaminodiol dipeptide isostere by epoxyamine cyclization
| Autor: | Stefano Norbedo, Fabio Benedetti, Francesca Dinon, Federico Berti, Giorgio Nardin |
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| Přispěvatelé: | Benedetti, Fabio, Berti, Federico, Dinon, Francesca, Nardin, Giorgio, Norbedo, Stefano |
| Jazyk: | angličtina |
| Rok vydání: | 2004 |
| Předmět: |
chemistry.chemical_classification
Dipeptide Peptidomimetic Stereochemistry Isostere Organic Chemistry Ring (chemistry) Aza Michael Aminoacid Conjugate Addition Stereoselective Azide Biochemistry Asymmetric induction Pyrrolidine Stereocenter Amino acid chemistry.chemical_compound chemistry Physical and Theoretical Chemistry |
| Popis: | [reaction: see text] The stereoselective synthesis of a novel proline-containing dipeptide isostere is described. Starting from l-valine, three new contiguous stereocenters are generated by asymmetric induction and epoxide chemistry, while the pyrrolidine ring of proline is introduced in the final step via intramolecular ring opening of the amino acid derived epoxyamine. Proline-containing peptidomimetics are potentially attractive as selective inhibitors of proline-specific enzymes, such as PPIases and retroviral proteases, and as analogues of bioactive peptides. |
| Databáze: | OpenAIRE |
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