Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: synthesis of N-acyl glycinals.
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.
Aneetha
Halikhedkar
H
The Gill Center for Biomolecular Science, Indiana University, Bloomington, IN 47405, USA. ahalikhe@indiana.edu
O'Dell
David K
DK
Tan
Bo
B
Walker
J Michael
JM
Hurley
Thomas D
TD
D000426:Alcohol Dehydrogenase / Q000378:metabolism*; D001095:Arachidonic Acids / Q000378:metabolism*; D002384:Catalysis; D063388:Endocannabinoids; D005998:Glycine / Q000096:biosynthesis*; D006801:Humans; D053858:Metabolic Networks and Pathways; D010084:Oxidation-Reduction; D053284:Polyunsaturated Alkamides / Q000378:metabolism*
D001095:Arachidonic Acids; D063388:Endocannabinoids; D053284:Polyunsaturated Alkamides; D000426:Alcohol Dehydrogenase; D005998:Glycine; C078814:anandamide