Velasco-Torrijos, Trinidad and Abbey, Lorna and O'Flaherty, Roisin
(2012)
A Concise Synthesis of Glycolipids Based on Aspartic Acid Building Blocks.
Molecules, 17.
pp. 11346-11362.
ISSN 1420-3049
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
|
| Keywords: |
synthetic glycolipids; glycosylated amino acids; glycomimetics; aspartic acid;
racemization; |
| Academic Unit: |
Faculty of Science and Engineering > Chemistry |
| Item ID: |
15030 |
| Identification Number: |
https://doi.org/10.3390/molecules171011346 |
| Depositing User: |
Roisin O'Flaherty
|
| Date Deposited: |
16 Nov 2021 15:07 |
| Journal or Publication Title: |
Molecules |
| Publisher: |
MDPI |
| Refereed: |
Yes |
| URI: |
|
| 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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