The synthesis of two oligomers, of a bifunctional diketopiperazine scaffold DKP-1, formally derived from the cyclization of l-aspartic acid and (S)-2,3-diaminopropionic acid, is reported. A trimeric and a tetrameric structure were prepared by solution-phase peptide synthesis (Boc strategy). Conformational analysis of these derivatives was carried out by a combination of 1H NMR spectroscopy, CD spectroscopy, and molecular modeling, and revealed the formation of β-bend ribbon involving 10-membered H-bonded rings and a reverse turn of the growing peptide chain.
Foldamers of bifunctional diketopiperazines displaying a beta-bend ribbon structure / R. Delatouche, M. Durini, M. Civera, L. Belvisi, U. Piarulli. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 51:32(2010), pp. 4278-4280.
Foldamers of bifunctional diketopiperazines displaying a beta-bend ribbon structure
M. Civera;L. BelvisiPenultimo
;
2010
Abstract
The synthesis of two oligomers, of a bifunctional diketopiperazine scaffold DKP-1, formally derived from the cyclization of l-aspartic acid and (S)-2,3-diaminopropionic acid, is reported. A trimeric and a tetrameric structure were prepared by solution-phase peptide synthesis (Boc strategy). Conformational analysis of these derivatives was carried out by a combination of 1H NMR spectroscopy, CD spectroscopy, and molecular modeling, and revealed the formation of β-bend ribbon involving 10-membered H-bonded rings and a reverse turn of the growing peptide chain.Pubblicazioni consigliate
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