A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks

doi:10.3390/molecules171011346

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Molecules 2012, 17(10), 11346-11362; doi:10.3390/molecules171011346

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A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks

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

Department of Chemistry, National University of Ireland Maynooth, Co. Kildare, Ireland ^† These authors contributed equally to this work.

* Author to whom correspondence should be addressed.

Received: 31 July 2012; in revised form: 15 September 2012 / Accepted: 21 September 2012 / Published: 25 September 2012

(This article belongs to the Special Issue Advances in Carbohydrate Chemistry)

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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.

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

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Cite This Article

MDPI and ACS Style

Velasco-Torrijos, T.; Abbey, L.; O’Flaherty, R. A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks. Molecules 2012, 17, 11346-11362.

AMA Style

Velasco-Torrijos T, Abbey L, O’Flaherty R. A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks. Molecules. 2012; 17(10):11346-11362.

Chicago/Turabian Style

Velasco-Torrijos, Trinidad; Abbey, Lorna; O’Flaherty, Roisin. 2012. "A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks." Molecules 17, no. 10: 11346-11362.

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