Open AccessNon-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.