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Synthesis and conformational study of novel pyrazine-based pseudopeptides bearing amidoxime, amidoxime ester and 1,2,4-oxadiazole units

Abstract : An efficient synthesis of pyrazine-based amidoximes bearing amino acid residues is reported. Esterification of amidoximes with further microwave-assisted cyclization into alpha-amino acid-derived 1,2,4-oxadiazoles has been developed. Conformational analysis of the obtained pseudopeptides by NMR and FTIR spectroscopy revealed intramolecular interactions due to the influence of a pyrazine ring and prolyl amide bond isomerization. The content of trans/cis conformers depending on the substitution at the pyrazine moiety for Pro-containing derivatives has been estimated.
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https://hal.univ-lorraine.fr/hal-01497718
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Submitted on : Wednesday, March 29, 2017 - 10:46:31 AM
Last modification on : Tuesday, March 30, 2021 - 3:24:38 AM

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Olga V. Ovdiichuk, Olga V. Hordiyenko, Axelle Arrault. Synthesis and conformational study of novel pyrazine-based pseudopeptides bearing amidoxime, amidoxime ester and 1,2,4-oxadiazole units. Tetrahedron, Elsevier, 2016, 72 (24), pp.3427-3435. ⟨10.1016/j.tet.2016.04.069⟩. ⟨hal-01497718⟩

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