A very efficient synthesis of orthogonally protected 1H-azepine-4-amino-4-carboxylic acid, abbreviated as Azn, a conformationally restricted analogue of ornithine, was realized. It was obtained on a gram scale in good overall yield in five steps, three of which did not require isolation of the intermediates, starting from the readily available 1-amino-4-oxo-cyclohexane-4-carboxylic acid. Both enantiomers were used for the preparation of pentapeptide models containing Ala, Aib, and Azn. Conformational studies using both spectroscopic techniques (NMR, CD) and molecular dynamics on model 5-mer peptides showed that the (R)-Azn isomer possesses a marked helicogenic effect.

1H-Azepine-4-amino-4-carboxylic Acid: A New α,α-Disubstituted Ornithine Analogue Capable of Inducing Helix Conformations in Short Ala-Aib Pentapeptides / S. Pellegrino, A. Contini, F. Clerici, A. Gori, D. Nava, M.L. Gelmi. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 18:28(2012 Jul), pp. 8705-8715.

1H-Azepine-4-amino-4-carboxylic Acid: A New α,α-Disubstituted Ornithine Analogue Capable of Inducing Helix Conformations in Short Ala-Aib Pentapeptides

S. Pellegrino
;
A. Contini
Secondo
;
F. Clerici;A. Gori;D. Nava
Penultimo
;
M.L. Gelmi
Ultimo
2012-07

Abstract

A very efficient synthesis of orthogonally protected 1H-azepine-4-amino-4-carboxylic acid, abbreviated as Azn, a conformationally restricted analogue of ornithine, was realized. It was obtained on a gram scale in good overall yield in five steps, three of which did not require isolation of the intermediates, starting from the readily available 1-amino-4-oxo-cyclohexane-4-carboxylic acid. Both enantiomers were used for the preparation of pentapeptide models containing Ala, Aib, and Azn. Conformational studies using both spectroscopic techniques (NMR, CD) and molecular dynamics on model 5-mer peptides showed that the (R)-Azn isomer possesses a marked helicogenic effect.
conformation analysis ; helical structures ; molecular dynamics ; peptidomimetics ; protein folding
Settore CHIM/06 - Chimica Organica
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/174343
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