Biocatalyzed Regioselective Synthesis in Undergraduate Organic Laboratories: Multistep Synthesis of 2-Arachidonoylglycerol

• Meghan R. Johnston ^[1] ; Alexandros Makriyannis ^[2] ; Kyle M. Whitten ^[2] ; Olivia C. Drew ^[1] ; Fiona A. Best ^[1]
  1. [1] Manhattanville College

     Manhattanville College

     Town of Harrison, Estados Unidos

     
  2. [2] Northeastern University, United States
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 93, Nº 12, 2016, págs. 2080-2083
• Idioma: inglés
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• Resumen

  • In order to introduce the concepts of biocatalysis and its utility in synthesis to organic chemistry students, a multistep synthesis of endogenous cannabinergic ligand 2-arachidonoylglycerol (2-AG) was tailored for use as a laboratory exercise. Over four weeks, students successfully produced 2-AG, purifying and characterizing products at each stage of the reaction series. This synthetic series also reinforces the importance of executing reactions under inert atmosphere, the strategic placement of protecting groups, and regioselectivity.