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:	http://www.mdpi.com/journal/molecules
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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