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Synthesis of 15 N‐, 13 C‐, and 2 H‐labeled methanandamide analogs
Author(s) -
Yao FenMei,
Palmer Sonya L.,
Khanolkar Atmaram D.,
Tian Xiaoyu,
Guo Jianxin,
Makriyannis Alexandros
Publication year - 2003
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.650
Subject(s) - anandamide , chemistry , cannabinoid , stereochemistry , nuclear magnetic resonance spectroscopy , cannabinoid receptor , arachidonic acid , ligand (biochemistry) , biochemistry , antagonist , receptor , enzyme
Four isotopically labeled, metabolically stable analogs of arachidony‐lethanolamide (anandamide), an endogenous cannabinoid ligand, were synthesized via a five‐step reaction sequence starting from arachidonic acid. These stable methanandamide derivatives will serve as probes for studying the conformational properties of anandamide in model membrane systems using solid‐state NMR spectroscopy. The synthetic methods described can be applied to the preparations of other anandamide analogs with isotopic labeling in different positions of the molecule, which could be utilized in biochemical and pharmacological experiments. Copyright © 2002 John Wiley & Sons, Ltd.