New developments in the synthesis of pyrrolizidinone-based dipeptide isosteres |
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Authors: | Maria Salvati Federica Pisaneschi |
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Institution: | Dipartimento di Chimica Organica ‘Ugo Schiff’, Università degli Studi di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy |
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Abstract: | 1,3-Dipolar cycloaddition of acrylamide with the cyclic nitrone derived from proline tert-butyl ester has been employed in the synthesis of bicyclic Gly-(s-cis)Pro isosteres suitably protected for the Fmoc-based solid phase peptide synthesis. (R)-1-Phenylethylamine was introduced as chiral auxiliary to resolve racemic intermediates and obtain enantiopure compounds. Using methacrylamide as dipolarophile, the analogous Ala-Pro mimetics have been prepared in racemic form, whereas the same strategy applied to methyl itaconate failed to give the corresponding Asp-Pro mimetic. |
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Keywords: | Nitrone 1 3-Dipolar cycloaddition Lactam Constrained amino acid Peptidomimetic |
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