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Velasco-Torrijos, Trinidad, 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 |
| Related URLs: | |
| URI: | https://mu.eprints-hosting.org/id/eprint/4253 |
| 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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