Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond

Synthesis and conformational behavior of pseudopeptides containing delta-azaproline. A cis conformational preference for Xaa(1)-delta-azaPro bond

delta-Azaproline, a new bis-nitrogen proline surrogate has been used in order to control the conformation of an AA-Psi Pro bond. Conformational analysis of Xaa(1)-delta-azaPro-Xaa(3) performed by NMR, IR experiments, and molecular modeling revealed a preference for a trans conformation of the Xaa(1)...

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Veröffentlicht in:Tetrahedron 2014-01, Vol.70 (2), p.363-370
Hauptverfasser: Humbert-Voss, Emelyne, Arrault, Axelle, Jamart-Grégoire, Brigitte
Format: Artikel
Sprache:eng
Schlagworte:
Chemical Sciences
Organic chemistry
Polymers
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Zusammenfassung:delta-Azaproline, a new bis-nitrogen proline surrogate has been used in order to control the conformation of an AA-Psi Pro bond. Conformational analysis of Xaa(1)-delta-azaPro-Xaa(3) performed by NMR, IR experiments, and molecular modeling revealed a preference for a trans conformation of the Xaa(1)-delta-azaPro bond when delta-azaPro is protected by a Boc group. The removal of the Boc protection leads to the establishment of a C-10 pseudocycle via a hydrogen bond network favoring the cis conformation of the Xaa(1)-delta-azaPro bond.
ISSN:0040-4020
DOI:10.1016/j.tet.2013.11.049