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Synthesis of 15N-, 13C-, and 2H-labeled methanandamide analogs

✍ Scribed by Fen-Mei Yao; Sonya L. Palmer; Atmaram D. Khanolkar; Xiaoyu Tian; Jianxin Guo; Alexandros Makriyannis

Publisher
John Wiley and Sons
Year
2003
Tongue
French
Weight
145 KB
Volume
46
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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.

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