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Facile transformation of glutamic acid into proline residue inside a tripeptide backbone
Authors:Adriano Mollica  Federica Feliciani  Ivana Cacciatore  Gino Lucente
Institution:a Dipartimento di Scienze del Farmaco, Università di Chieti-Pescara ‘G. d’Annunzio’, Via dei Vestini 31, 66100 Chieti, Italy
b Dipartimento di Chimica e Tecnologie del Farmaco, ‘Sapienza’, Università di Roma, P.le A. Moro 5, 00185 Roma, Italy
Abstract:In this Letter we present a simple reaction pathway which allows the conversion of the glutamic acid residue of a tripeptide into a proline residue. The reaction was performed by using Boc-Val-Glu-Phe-NH2 as a starting material and is based on a NaH-induced intraresidue alkylation under reaction conditions analogous to that adopted during the Freidinger lactams formation.
Keywords:δ-Lactam-constrained peptides  Glutamic acid  Peptides  Proline
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