Alcohol dehydrogenase-catalyzed in vitro oxidation of anandamide to N-arachidonoyl glycine, a lipid mediator: Synthesis of N-acyl glycinals

被引：17

作者：

Aneetha, Halikhedkar ^{[1
,2
]}

O'Dell, David K. ^{[1
,2
]}

Tan, Bo ^{[1
,2
]}

Walker, J. Michael ^{[1
,2
]}

Hurley, Thomas D. ^{[3
]}

机构：

[1] Indiana Univ, Gill Ctr Biomol Sci, Bloomington, IN 47405 USA

[2] Indiana Univ, Dept Psychol & Brain Sci, Bloomington, IN 47405 USA

[3] Indiana Univ, Sch Med, Dept Biochem & Mol Biol, Indianapolis, IN 46202 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 01期

关键词：

Anandamide; Cannabinoids; Cannabinoid receptors; N-Arachidonoyl glycinal; N-Arachidonoyl glycine; N-Arachidonoyl ethanolamide; AMINO-ACID-SEQUENCE; ARACHIDONYLETHANOLAMIDE ANANDAMIDE; CANNABINOID RECEPTORS; BRAIN; ETHANOLAMINE; LIVER; IDENTIFICATION; BIOSYNTHESIS; ISOZYMES; ARACHIDONYLGLYCINE;

D O I：

10.1016/j.bmcl.2008.10.087

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

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. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：237 / 241

页数：5

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