✦ LIBER ✦
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
✍ Scribed by Els Mannekens; Marco Crisma; Sylvia Van Cauwenberghe; Dirk Tourwé
- Publisher
- John Wiley and Sons
- Year
- 2003
- Tongue
- English
- Weight
- 175 KB
- Volume
- 2003
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
Abstract
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)