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. [10.1021/acs.orglett.0c02331]
Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer
Vaghi, Francesco;Bucci, Raffaella;Clerici, Francesca;Contini, Alessandro;Gelmi, Maria Luisa
2020-07-30
Abstract
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.
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