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

Publikováno v: Tetrahedron. 65:2266-2278

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 diffe

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::ea8f9428c0c27c743eed1c794b2a3d49
https://doi.org/10.1016/j.tet.2009.01.057

Synthesis of 4-amino-3-oxo-tetrahydroazepino[3,4-b]indoles: new conformationally constrained Trp analogs

Autor: Debby Feytens, Dirk Tourwé, Nga N. Chung, Aleksandra Misicka, Karolina Pulka, Andrzej W. Lipkowski, Rien De Wachter, Piotr Kosson, Isabelle Van den Eynde, Peter W. Schiller

Publikováno v: Tetrahedron. 63:1459-1466

The synthesis of tryptophan analogs is reported in which the conformation has been constrained by formation of a seven-membered lactam. Boc-protected 2′-formyl tryptophan was obtained by SeO2 oxidation of Boc-tetrahydro-β-carboline-3-carboxylic ac

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_________::584ff2df4821429e45e0196321acf1ca
https://doi.org/10.1016/j.tet.2006.11.069

Synthesis, biological evaluation, and automated docking of constrained analogues of the opioid peptide H-Dmt-d-Ala-Phe-Gly-NH 2 using the 4- or 5-methyl substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold

Autor: Chris de Graaf, Didier Rognan, Rien De Wachter, Atilla Keresztes, Bart Vandormael, Dirk Tourwé, Steven Ballet, Géza Tóth

Publikováno v: Wachter, R D, De Graaf, C, Keresztes, A, Vandormael, B, Ballet, S, Tóth, G, Rognan, D & Tourwé, D 2011, ' Synthesis, biological evaluation, and automated docking of constrained analogues of the opioid peptide H-Dmt-d-Ala-Phe-Gly-NH 2 using the 4-or 5-methyl substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold ', Journal of Medicinal Chemistry, vol. 54, no. 19, pp. 6538-6547 . https://doi.org/10.1021/jm2003574
Journal of Medicinal Chemistry, 54(19), 6538-6547. American Chemical Society

The Phe 3 residue of the N-terminal tetrapeptide of dermorphin (H-Dmt-d-Ala-Phe-Gly-NH 2) was conformationally constrained using 4- or 5-methyl-substituted 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one (Aba) stereoisomeric scaffolds. Several of the s

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c72007ca2dedd6847e8aca2ffe1fe0f1
https://hdl.handle.net/1871.1/0851b08b-395d-40f7-be6f-a57d3e5550d9

Asymmetric synthesis and conformational analysis by NMR spectroscopy and MD of Aba- and α-MeAba-containing dermorphin analogues

Autor: Dirk Tourwé, Jayapal Reddy Mallareddy, Steven Ballet, José C. Martins, Rien De Wachter, Attila Keresztes, Fanni Tóth, Géza Tóth, Pieter M. S. Hendrickx, Bart Vandormael

Publikováno v: ChemMedChem. 6(11)

Dermorphin analogues, containing a (S)- and (R)-4-amino1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold (Aba) and the alpha-methylated analogues as conformationally constrained phenylalanines, were prepared. Asymmetric phase-transfer catalysis was unab

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::b76fc20cfe382d0a765544fa5aa23539
https://pubmed.ncbi.nlm.nih.gov/21990068

High-performance liquid chromatographic separation of stereoisomers of N-phthaloyl-protected amino acids and dipeptidomimetics

Autor: Antal Péter, István Ilisz, Karolien Van Rompaey, Rien De Wachter, Dirk Tourwé, Steven Ballet, Daniel W. Armstrong

Publikováno v: Journal of separation science. 30(12)

The stereoisomers of N-phthaloyl-protected amino acids and dipeptidomimetics were separated on macrocyclic glycopeptide and cellulose-based chiral stationary phases (CSPs) in the RP and polar-ionic modes. The effects of the organic modifier, the mobi

Externí odkaz: https://explore.openaire.eu/search/publication?articleId=doi_dedup___::cecc746fb68c54b5127b44aaf923daa0
https://pubmed.ncbi.nlm.nih.gov/17638345