A new non-natural β-amino acid, named 3-Ar-β-Morph, was designed and synthesized via a regio- and diastereoselective Pd-catalyzed C(sp3)H-arylation of the corresponding 2S,6S-(6-methoxymorpholin-2-yl)carboxylic acid, readily available from glucose. According to the computational prevision and confirmed by IR and NMR data, the insertion of 3-Ar-β-Morph in a model foldamer represents a way to stabilize a PPII-like helix through the presence of two γ-turns, secondary structure motifs induced by the morpholine ring, and the trans-tertiary amide bond.
Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer / F. Vaghi, R. Bucci, F. Clerici, A. Contini, M.L. Gelmi. - In: ORGANIC LETTERS. - ISSN 1523-7060. - 22:15(2020 Jul 30), pp. 6197-6202.
Titolo: | Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer |
Autori: | GELMI, MARIA LUISA (Corresponding) |
Parole Chiave: | Foldamers, Amides, Peptides and proteins,Conformation,Cluster chemistry |
Settore Scientifico Disciplinare: | Settore CHIM/06 - Chimica Organica |
Data di pubblicazione: | 30-lug-2020 |
Rivista: | |
Tipologia: | Article (author) |
Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acs.orglett.0c02331 |
Appare nelle tipologie: | 01 - Articolo su periodico |
File in questo prodotto:
File | Descrizione | Tipologia | Licenza | |
---|---|---|---|---|
Postprint_OL_Gelmi_2020.pdf | Post-print, accepted manuscript ecc. (versione accettata dall'editore) | Embargo: 30/07/2021 Richiedi una copia | ||
acs.orglett.0c02331.pdf | Publisher's version/PDF | Administrator Richiedi una copia |