Please use this identifier to cite or link to this item: http://hdl.handle.net/2440/47168
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Type: Journal article
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
Ballet, Steven
Tomboly, Csaba
De Wachter, Rien
Vanommeslaeghe, Kenno
Biesemans, Monique
Willem, Rudolph
Tourwe, Dirk
Citation: European Journal of Organic Chemistry, 2006; 13:2899-2911
Publisher: Wiley-VCH
Issue Date: 2006
ISSN: 1434-193X
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.
RMID: 0020082061
DOI: 10.1002/ejoc.200500996
Published version: http://www3.interscience.wiley.com/journal/112594360/abstract
Appears in Collections:Chemistry and Physics publications

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