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N-amino et hydrazino peptides : aspects chimiques et structuraux

Abstract : In principe, the substitution of an [alpha]-hydrazino for an [beta]-amino acid residue in peptide analogues can give two different peptide bond surrogate : the hydrazide bond (CO-NH-NH), which is most often obtained, and the N-amino amide (CO-N(NH2) pepti-dominmec bond. A strategy for the selective synthesis of each surrogate has been worked out and applied to methythydrazine and to ethyl hydrazino acetate, a derivative of the hydrazinic analogue of the simplest coded [beta]-amino acid, namely glycine. These two modified their intrinsic structural properties, the interactions in which they can be involved, and their conformational impact on both folded structures. The conformational analyses have been carried out by IR and NMR spectro-scopy (solution state), and by X-ray diffraction on single crystals (solid state). A cyclic structural mimic of the [alpha]-turn, including an [beta]-hydrazino acid residue, has also been designed
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Alain Lecoq. N-amino et hydrazino peptides : aspects chimiques et structuraux. Autre. Institut National Polytechnique de Lorraine, 1991. Français. ⟨NNT : 1991INPL045N⟩. ⟨tel-01752141⟩



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