Peptides containing variations of the β-amyloid hydrophobic core and five-membered sulfamidates derived from β-amino acid α-methylisoserine have been synthesized and fully characterized in the gas phase, solid state and in aqueous solution by a combination of experimental and computational techniques. The cyclic sulfamidate group effectively locks the secondary structure at the N-terminus of such hybrid peptides imposing a conformational restriction and stabilizing non-extended structures. This conformational bias, which is maintained in the gas phase, solid state and aqueous solution, is shown to be resistant to structure templating through assays of in vitro β-amyloid aggregation, acting as β-sheet breaker peptides with moderate activity.

Mazo, N., Navo, C., Peccati, F., Andreo, J., Airoldi, C., Goldsztejn, G., et al. (2023). Conformationally Restricted β-Sheet Breaker Peptides Incorporating Cyclic α-Methylisoserine Sulfamidates. CHEMISTRY-A EUROPEAN JOURNAL, 29(9 (February 10, 2023)) [10.1002/chem.202202913].

Conformationally Restricted β-Sheet Breaker Peptides Incorporating Cyclic α-Methylisoserine Sulfamidates

Airoldi, Cristina;
2023

Abstract

Peptides containing variations of the β-amyloid hydrophobic core and five-membered sulfamidates derived from β-amino acid α-methylisoserine have been synthesized and fully characterized in the gas phase, solid state and in aqueous solution by a combination of experimental and computational techniques. The cyclic sulfamidate group effectively locks the secondary structure at the N-terminus of such hybrid peptides imposing a conformational restriction and stabilizing non-extended structures. This conformational bias, which is maintained in the gas phase, solid state and aqueous solution, is shown to be resistant to structure templating through assays of in vitro β-amyloid aggregation, acting as β-sheet breaker peptides with moderate activity.
Articolo in rivista - Articolo scientifico
hybrid peptides; sulfamidates; β-amino acids; β-amyloid; β-sheet breaker peptides;
English
15-nov-2022
2023
29
9 (February 10, 2023)
e202202913
partially_open
Mazo, N., Navo, C., Peccati, F., Andreo, J., Airoldi, C., Goldsztejn, G., et al. (2023). Conformationally Restricted β-Sheet Breaker Peptides Incorporating Cyclic α-Methylisoserine Sulfamidates. CHEMISTRY-A EUROPEAN JOURNAL, 29(9 (February 10, 2023)) [10.1002/chem.202202913].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/396955
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