A Concise Synthesis of Glycolipids Based on Aspartic Acid Building BlocksReportar como inadecuado




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Department of Chemistry, National University of Ireland Maynooth, Co. Kildare, Ireland



These authors contributed equally to this work.





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Abstract 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. View Full-Text

Keywords: synthetic glycolipids; glycosylated amino acids; glycomimetics; aspartic acid; racemization synthetic glycolipids; glycosylated amino acids; glycomimetics; aspartic acid; racemization





Autor: Trinidad Velasco-Torrijos * , Lorna Abbey † and Roisin O’Flaherty †

Fuente: http://mdpi.com/



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