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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Tetrahedron, Elsevier, 2016, 72 (24), pp.3427-3435. 〈10.1016/j.tet.2016.04.069〉
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https://hal.univ-lorraine.fr/hal-01497718
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Soumis le : mercredi 29 mars 2017 - 10:46:31
Dernière modification le : mardi 24 juillet 2018 - 16:42:57

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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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