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    A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks


    Velasco-Torrijos, Trinidad and Abbey, Lorna and O'Flaherty, Roisin (2012) A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks. Molecules, 17 (10). pp. 11346-11362. ISSN 1420-3049

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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.

    Item Type: Article
    Additional Information: This article is available at doi:10.3390/molecules171011346 .Creative Commons Attribution License http://creativecommons.org/licenses/by/3.0/
    Keywords: synthetic glycolipids; glycosylated amino acids; glycomimetics; aspartic acid; racemization;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 4253
    Depositing User: Dr. Trinidad Velasco-Torrijos
    Date Deposited: 12 Mar 2013 16:40
    Journal or Publication Title: Molecules
    Publisher: MDPI
    Refereed: Yes
    URI:

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