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|Title:||Synthesis and evaluation of the β-turn properties of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones and of their spirocyclic derivative|
|Other Titles:||Synthesis and evaluation of the beta-turn properties of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones and of their spirocyclic derivative|
|Author:||Van Rompaey, Karolien|
De Wachter, Rien
|Citation:||European Journal of Organic Chemistry, 2006; 13:2899-2911|
|School/Discipline:||School of Chemistry and Physics : Chemistry|
|Abstract:||A series of 4-amino-tetrahydro-2-benzazepm-3-one derivatives (Ac-Aba-Xxx-NHMe) were prepared as tetrapeptide mimetics. Considering the structural resemblance with the so-called Freidinger lactams, their propensity to adopt a β-turn conformation was investigated by NMR spectroscopy (solvent and temperature dependence) and molecular modeling. Interestingly, most of these lactams adopt extended conformations, only the spiro-benzazepinone 9 has a strong preference for the formation of a β-turn.|
|Appears in Collections:||Chemistry and Physics publications|
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