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Oxa-diketopiperazines: Access and Conformational Analysis of Potential Turn Inducers

Abstract : An improvement of the 1,2,5‐oxadiazine‐3,6‐diones (Oxd) synthesis and reactivity is described in this paper. The methodology has been successfully applied to produce a library of this poorly studied scaffold, which can be considered as an oxa‐diketopiperazine (oxa‐DKP). Significantly, the first crystal structures of oxa‐DKP were obtained and compared to the diketopiperazine ring. Finally, a straightforward procedure concerning the coupling of various amino acids with oxa‐DKP heterocycles to afford original peptidomimetics was reported. The conformational analysis realized on di‐ and tripeptide analogs revealed that the oxa‐DKP skeleton exhibited remarkable β‐turn inducer properties.
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https://hal-univ-lemans.archives-ouvertes.fr/hal-02313808
Contributeur : Arnaud Martel <>
Soumis le : vendredi 11 octobre 2019 - 15:15:21
Dernière modification le : mercredi 25 mars 2020 - 09:21:38

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Mathéo Berthet, Aurélien Lebrun, Arnaud Martel, Thomas Cheviet, Jean Martinez, et al.. Oxa-diketopiperazines: Access and Conformational Analysis of Potential Turn Inducers. ChemistrySelect, Wiley, 2017, 2 (21), pp.5824-5827. ⟨10.1002/slct.201701393⟩. ⟨hal-02313808⟩

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