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Oxa–diketopiperazines: Access and Conformational Analysis of Potential Turn Inducers
Author(s) -
Berthet Mathéo,
Lebrun Aurélien,
Martel Arnaud,
Cheviet Thomas,
Martinez Jean,
Parrot Isabelle
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701393
Subject(s) - tripeptide , diketopiperazines , peptidomimetic , turn (biochemistry) , chemistry , stereochemistry , inducer , combinatorial chemistry , ring (chemistry) , confusion , amino acid , dipeptide , peptide , biochemistry , psychology , organic chemistry , gene , psychoanalysis
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.