A concise synthesis of glycolipids based on aspartic acid building blocks.

L-aspartic acid building blocks bearing galactosyl moieties were used to synthesise glycolipid mimetics of variable hydrocarbon chain length. The glycolipids were readily prepared through amide bond formation using the TBTU/HOBt coupling methodology. It was observed that, under these conditions, activation of the α-carboxylic acid of the intermediates led to near complete racemisation of the chiral centre if the reaction was carried out in the presence of a base such as triethylamine. The enantiomerically pure glycolipids were obtained after careful consideration of the synthetic sequence and by performing the coupling reactions in the absence of base.

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Trinidad Velasco-Torrijos, Lorna Abbey, Roisin O'Flaherty. A concise synthesis of glycolipids based on aspartic acid building blocks. Molecules (Basel, Switzerland). 2012 Sep 25;17(10):11346-62

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PMID: 23011277

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