Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments

A series of triazole-linked ester-type glycolipids were efficiently prepared via a two-step sequence involving microwave accelerated 'click' chemistry and debenzylation. All carbon chain length varied O-alkynyl fatty esters used to couple with 1-azido-tetra-O-benzyl-β-d-glucoside showed excellent tolerance to the microwave-assisted 1,3-dipolar cycloaddition (click reaction), forming the unique cycloadducts in almost quantitative yields of 92.9-99.0% within a quarter. The desired glycolipids were then readily afforded via the successive hydrogenolysis promoted by PdCl2/H2. Their adsorption competence on gold electrode were evaluated through EIS (electrochemical impedance spectroscopy) measurement and the resulting structure-activity relationship (SAR) was discussed. In addition, the cytotoxicity of this triazolyl glycolipid class on HeLa (cervix cancer) cell line was identified by MTT assay.

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