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Synthesis of 15 N and 13 C selectively labeled anandamide
Author(s) -
Xie XiangQun,
Yang Hongqin,
Choi Greg,
Lin Sunyuan,
Makriyannis Alexandros
Publication year - 2002
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.601
Subject(s) - anandamide , chemistry , cannabinoid receptor , endocannabinoid system , ligand (biochemistry) , cannabinoid , stereochemistry , binding affinities , combinatorial chemistry , chemical synthesis , receptor , biochemistry , in vitro , agonist
Anandamide (Figure 1a) (arachidonyl ethanolamide, AEA), (5Z,8Z,11Z,14Z)‐N‐(2‐hydroxyethyl)‐5,8,11,14‐Eicosatetraenamide, is an endogenous cannabinoid ligand possessing important biological activity. The conformation of AEA in its native receptor binding environment is particularly of interest for pharmaceutical research and biochemistry in general. Here we report a novel synthetic pathway, which selectively introduces 15 N and 13 C isotopes into the anandamide molecule. This isotopically labeled AEA can be studied conformationally in its native binding condition via solid state NMR. These synthetic procedures can also be adapted to produce radioactive ligands for receptor binding assays and other structural studies. Copyright © 2002 John Wiley & Sons, Ltd.