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
Rok vydání:	2007
Předmět:	chemistry.chemical_classification Sodium cyanoborohydride Stereochemistry Organic Chemistry Tryptophan Ring (chemistry) Biochemistry Reductive amination Amino acid chemistry.chemical_compound chemistry Drug Discovery Lactam Opioid peptide Derivative (chemistry)
Zdroj:	Tetrahedron. 63:1459-1466
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.11.069
Popis:	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 acid. Reductive amination was performed with a variety of amines and amino acid esters using sodium cyanoborohydride, followed by ring closure to the target compounds. The constrained Trp derivative has been incorporated into the endomorphin-1 opioid peptide sequence to probe the bioactive conformation.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::584ff2df4821429e45e0196321acf1ca https://doi.org/10.1016/j.tet.2006.11.069 Zobrazit plný text záznamu Full Text from ScienceDirect