Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer | Zendy

Francesco Vaghi | Zendy; Raffaella Bucci | Zendy; Francesca Clerici | Zendy; Alessandro Contini | Zendy; Maria Luisa Gelmi | Zendy

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Non-natural 3-Arylmorpholino-β-amino Acid as a PPII Helix Inducer

Author(s) -

Francesco Vaghi,

Raffaella Bucci,

Francesca Clerici,

Alessandro Contini,

Maria Luisa Gelmi

Publication year - 2020

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.0c02331

Subject(s) - chemistry , morpholine , stereochemistry , amide , foldamer , polyproline helix , ring (chemistry) , helix (gastropod) , amino acid , medicinal chemistry , organic chemistry , peptide , biochemistry , ecology , snail , biology

A new non-natural β-amino acid, named 3-Ar-β-Morph, was designed and synthesized via a regio- and diastereoselective Pd-catalyzed C(sp 3 )H-arylation of the corresponding 2 S ,6 S -(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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