Influence of ring substitution on the conformation and β-turn mimicry of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one peptide mimetics

Autor:	Zofia Urbańczyk-Lipkowska, Rien De Wachter, Debby Feytens, Isabelle Van den Eynde, Steven Ballet, Attila Keresztes, Géza Tóth, Dirk Tourwé, Luc Brans
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Tetrapeptide Molecular model Chemistry Peptidomimetic Stereochemistry Organic Chemistry Substituent Peptide Dermorphin Ring (chemistry) Biochemistry Turn (biochemistry) chemistry.chemical_compound Drug Discovery
Zdroj:	Tetrahedron. 65:2266-2278
ISSN:	0040-4020
DOI:	10.1016/j.tet.2009.01.057
Popis:	Analogs of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones, containing a methyl substituent at the 4- or 5-position, or a phenyl substituent at C-1, were prepared. Conformational analysis of tetrapeptide models containing these analogs indicated different conformations of the benzazepinone ring, and extended backbone conformations, except for the 4-methyl-substituted analog. The latter was shown to have a strong preference for a turn conformation. Incorporation into the N-terminal tetrapeptide sequence of dermorphin resulted in potent opioid analogs and an indication that the receptor-bound conformation might not adopt a turn structure.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ea8f9428c0c27c743eed1c794b2a3d49 https://doi.org/10.1016/j.tet.2009.01.057 Zobrazit plný text záznamu Full Text from ScienceDirect