Mechanochemical Multistep Approach to Diacylglycerols

  • Author:
  • Published: 08 April 2019
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Beilstein Journal of Organic Chemistry/Beilstein-Institut
thumbnail image: Mechanochemical Multistep Approach to Diacylglycerols

Mechanochemical methods use mechanical energy, such as compression, shear, or friction, for chemical transformations. They have great potential for use in solvent-free synthesis. The use of ball milling techniques has extended its application to the synthesis of architecturally complex targets. Many biologically building blocks, such as amino acids, peptides, saccharides, nucleotides, and nucleosides, have been prepared by mechanochemical synthesis. However, mechanosynthesis of lipids by ball milling techniques has remained essentially unexplored.

José G. Hernández and Carsten Bolm, RWTH Aachen University, Germany, and colleagues have developed a mechanochemical multistep synthetic route to mono- and diacylglycerol derivatives. The team started with glycidol (pictured) and added a hydroxy protecting group. This step is followed by a metal-catalyzed epoxide-ring opening and the solvent-free ester formation between monoacylglycerols and fatty acids to afford diacylglycerols (DAGs).

DAGs are glycerolipids containing two fatty acids esterified to the alcohol glycerol. They are important due to their signaling functions in cells. Biological routes to form DAGs include enzymatic degradation of glycerophospholipids and lipolysis of triacylglycerols (TAGs). However, due to the structural diversity of fatty acids present in acylglycerols and to the small structural differences among these fatty acids (e.g., chain length, degree of unsaturation, double bond position, stereochemistry), the access to pure DAGs and TAGs from natural sources by extraction is inconvenient. An alternative chemical synthesis starting from glycerol or glycidol involves multiple preparative steps in organic solvents, e.g., CH2Cl2, THF, Et2O.

Article Views: 1244

Sign in Area

Please sign in below

Additional Sign In options

Please note that to comment on an article you must be registered and logged in.
Registration is for free, you may already be registered to receive, e.g., the newsletter. When you register on this website, please ensure you view our terms and conditions. All comments are subject to moderation.

Article Comments - To add a comment please sign in

Bookmark and Share

If you would like to reuse any content, in print or online, from, please contact us first for permission. more

CONNECT: on Facebook on Twitter on YouTube on LinkedIn Sign up for our free newsletter

Magazine of Chemistry Europe (16 European Chemical Societies)published by Wiley-VCH