1H-Azepine-2-oxo-5-amino-5-carboxylic Acid: A 3(10) Helix Inducer and an Effective Tool for Functionalized Gold Nanoparticles
Articolo
Data di Pubblicazione:
2015
Citazione:
1H-Azepine-2-oxo-5-amino-5-carboxylic Acid: A 3(10) Helix Inducer and an Effective Tool for Functionalized Gold Nanoparticles / S. Pellegrino, A. Bonetti, F. Clerici, A. Contini, A. Moretto, R. Soave, M.L. Gelmi. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 80:11(2015 Jun 05), pp. 5507-5516.
Abstract:
A new alpha,alpha-disubstituted constrained glutamine analogue has been designed to decorate gold nanopartides and to induce a 3(10)-helix when inserted in peptides. Using an efficient "one-pot" asymmetric Schmidt reaction between 4-disubstituted-cydohexanone and hydroxyalkylazides, 1H-azepine-2-oxo-5-amino-5-carboxylic acid was prepared. The main (R) isomer was inserted at the N-terminus in a very short peptide sequence (i.e., PhCO-(R)-Oxo-Azn-L-Ala-Aib-L-AlaNHMe) and a stable 3(10)-helix conformation was obtained, as verified by both NMR experiments and molecular dynamics (MD) simulations. Finally, the presence of the hydroxyl chain at the nitrogen atom of the ring allowed for the preparation of covered chiral gold nanopartides.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Asymmetric schmidt reaction; ring expansion reactions; alpha-amino-acids; drug-delivery; hydroxyalkyl azides; secondary structure; molecular-dynamics; optical-absorption; cation-PI; derivates
Elenco autori:
S. Pellegrino, A. Bonetti, F. Clerici, A. Contini, A. Moretto, R. Soave, M.L. Gelmi
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