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Nepogodiev, Sergey A., Fais, Margherita, Hughes, David L. and Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275
(2011)
Synthesis of apiose-containing oligosaccharide fragments of the plant cell wall: fragments of rhamnogalacturonan-II side chains A and B, and apiogalacturonan.
Organic & Biomolecular Chemistry, 9 (19).
pp. 6670-6684.
ISSN 1477-0520
Abstract
Fragments of pectic polysaccharides rhamnogalacturonan-II (RG-II) and apiogalacturonan were synthesised using p-tolylthio apiofuranoside derivatives as key building blocks. Apiofuranose thioglycosides can be conveniently prepared by cyclization of the corresponding dithioacetals possessing a 2,3-O-isopropylidene group, which is required for preservation of the correct (3R) configuration of the apiofuranose ring. The remarkable stability of this protecting group in apiofuranose derivatives requires its replacement with a more reactive protecting group, such as a benzylidene acetal which was used in the synthesis of trisaccharide β-Rhap-(1→3′)-β-Apif-(1→2)-α-GalAp-OMe. The X-ray crystal structure of the protected precursor of this trisaccharide has been elucidated.
| Item Type: | Article |
|---|---|
| Faculty \ School: | Faculty of Science > School of Chemistry (former - to 2024) |
| Depositing User: | Users 2731 not found. |
| Date Deposited: | 20 Mar 2012 12:16 |
| Last Modified: | 24 Sep 2024 08:59 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/38362 |
| DOI: | 10.1039/c1ob05587a |
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