Synthesis of acylglycerol derivatives by mechanochemistry

• Karen J. Ardila-Fierro,
• Andrij Pich,
• Marc Spehr,
• José G. Hernández and
• Carsten Bolm

Beilstein J. Org. Chem. 2019, 15, 811–817, doi:10.3762/bjoc.15.78

• ; diacylglycerols; lipids; mechanochemistry; Introduction In addition to being guided by chemical signals, cells respond to mechanical cues by sensing and transducing external mechanical inputs into biochemical and electrical signals [1]. Consequently, every time a cell is subjected to mechanical loads, the

• ]. Among the variety of amphipathic or hydrophobic small molecules that exhibit a lipid structure, diacylglycerols (DAGs) are important due to their signaling functions in cells (DAG signaling) [22][23][24]. Structurally, DAGs are glycerolipids containing two fatty acids esterified to the alcohol glycerol

• yields up to 91% (Scheme 4). Particularly interesting was the formation of DAG (18:0/20:4) 5d, an important lipidic backbone present in the biologically relevant phosphatidylinositol 4,5-bisphosphate (PIP2) [22]. In fact, diacylglycerols have proven to play vital roles in regulation of lipid bilayer and