Non-natural lipids: Synthesis and characterization of esters from meta-carborane-1-carboxylic acid

Add time:09/09/2019    Source:sciencedirect.com

Lipids are defined as apolar molecules comprising as major classes fatty acids and fatty acid esters of normally natural origin. Non-natural components, such as dicarba-closo-dodecaboranes (in short carboranes) can also form acids and esters, which reveal lipid-like properties. Carboranes are synthetic boron clusters featuring ten BH and two CH vertices, organized in icosahedral shape. The highly hydrophobic clusters are organic-inorganic hybrid constructs and can be modified at both the cluster boron and the cluster carbon atoms via adjusted organic reactions. Here, we report the synthesis and characterization of lipid esters from meta-carborane-1-carboxylic acid using a new coupling reagent strategy. Carboranyl esters from long-chain alcohols revealed wax-like properties.

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