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Synthesis and Conformational Analysis of 1:1 [α/α‐ N α ‐Bn‐Hydrazino] and 1:1 [α‐ N α ‐Bn‐Hydrazino/α] Trimers: Determination of the Δ δ Value for the γ‐Turn Structuration
Author(s) -
Romero Eugénie,
Moussodia RalphOlivier,
JamartGrégoire Brigitte,
Acherar Samir
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800755
Subject(s) - geminal , alternation (linguistics) , chemistry , foldamer , value (mathematics) , crystallography , computational chemistry , stereochemistry , mathematics , philosophy , linguistics , statistics
Heterogeneous 1:1 [α/α‐ N α ‐Bn‐hydrazino] pseudopeptides are able to self‐organize in CDCl 3 solution by an alternation of the γ‐turn and hydrazinoturn conformations. Amidation of the C terminus allowed us to calculate the difference in the chemical shift (Δ δ ) of the 1 H NMR signals of the geminal amidic protons and to associate a Δ δ value from 2.58 to 2.75 ppm with the presence of a hydrazinoturn at the C terminus. In this paper we wish to demonstrate that the measurement of a Δ δ value close to 0.9 ppm can be correlated with the presence of a γ‐turn structuration. This result will complete this valuable toolbox of Δ δ values for a rapid access to the self‐organization of pseudopeptides involving hydrazinoturns and/or γ‐turns based on simple and accessible 1 H NMR experiments, and should also provide an opportunity to extend the scope of heterogeneous backbone foldamer design.