Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals
| Autor: | Thomas D. Hurley, Halikhedkar Aneetha, David K. O’Dell, Bo Tan, J. Michael Walker |
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| Rok vydání: | 2009 |
| Předmět: |
Cannabinoid receptor
Polyunsaturated Alkamides Stereochemistry Clinical Biochemistry Glycine Pharmaceutical Science Arachidonic Acids Biochemistry Catalysis Article chemistry.chemical_compound Drug Discovery Humans Ethanolamide Molecular Biology Alcohol dehydrogenase biology Chemistry Organic Chemistry Alcohol Dehydrogenase Lipid signaling Anandamide Endocannabinoid system Metabolic pathway biology.protein Molecular Medicine lipids (amino acids peptides and proteins) Oxidation-Reduction Metabolic Networks and Pathways Endocannabinoids |
| Zdroj: | Bioorganic & Medicinal Chemistry Letters. 19:237-241 |
| ISSN: | 0960-894X |
| DOI: | 10.1016/j.bmcl.2008.10.087 |
| Popis: | N-arachidonoyl ethanolamide or anandamide is an endocannabinoid found in most tissues where it acts as an important signaling mediator in a number of physiological and pathophysiological processes. Consequently, intense effort has been focused on understanding all its biosynthetic and metabolic pathways. Herein we report human alcohol dehydrogenase-catalyzed sequential oxidation of anandamide to N-arachidonoyl glycine, a prototypical member of the class of long chain fatty acyl glycines, a new group of lipid mediators with a wide array of physiological effects. We also present a straightforward synthesis for a series of N-acyl glycinals including N-arachidonoyl glycinal, an intermediate in the alcohol dehydrogenase-catalyzed oxidation of anandamide. |
| Databáze: | OpenAIRE |
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