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

Halikhedkar Aneetha, David K. O'Dell, Bo Tan, J. Michael Walker, Thomas D. Hurley

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)237-241
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume19
Issue number1
DOIs
StatePublished - Jan 1 2009

    Fingerprint

Keywords

  • Anandamide
  • Cannabinoid receptors
  • Cannabinoids
  • N-Arachidonoyl ethanolamide
  • N-Arachidonoyl glycinal
  • N-Arachidonoyl glycine

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this