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 | Zendy

Mannekens Els | Zendy; Crisma Marco | Zendy; Van Cauwenberghe Sylvia | Zendy; Tourwé Dirk | Zendy

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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)

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