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Synthesis of 1‐( m ‐Hydroxybenzyl)‐Substituted 1,2,3,4‐Tetrahydroisoquinoline‐3‐carboxylic Acid Derivatives as Opioid Peptide Mimetics − Unexpected Amide Bond Cleavages under Mild Conditions
Author(s) -
Mannekens Els,
Crisma Marco,
Van Cauwenberghe Sylvia,
Tourwé Dirk
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300175
Subject(s) - chemistry , dipeptide , tetrahydroisoquinoline , amide , peptide bond , stereochemistry , carboxylic acid , stereoselectivity , ligand (biochemistry) , peptide , peptide synthesis , combinatorial chemistry , receptor , organic chemistry , catalysis , biochemistry
N ‐Glycyl‐(1 R ,3 S )‐1‐( m ‐hydroxybenzyl)‐1,2,3,4‐tetrahydroisoquinoline‐3‐carboxylic acid (Tic) was prepared as a Tyr‐Tic dipeptide mimetic for exploration of its potential as a delta opioid receptor selective ligand. The compound was successfully obtained by a stereoselective synthesis starting from L ‐Tic. In the course of the reactions, unusual peptide bond cleavages were observed under mild conditions, and reaction mechanisms have been proposed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)