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Chauvin, Anne Laure, Nepogodiev, Sergey A. and Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275
(2005)
Synthesis of a 2,3,4-triglycosylated rhamnoside fragment of rhamnogalacturonan-II side chain a using a late stage oxidation approach.
Journal of Organic Chemistry, 70 (3).
pp. 960-966.
ISSN 0022-3263
Abstract
(Chemical Equation Presented) Pectic polysaccharide RG-II, a key component of plant primary cell walls, is known to exist as a dimer formed by means of borate diester cross-links between apiosyl residues of one of its constituent side-chain oligosaccharides. Described herein is the strategy for the synthesis of the branched tetrasaccharide α-D-GalA-(1→2)-[β-D-GalA- (1→3)]-[α-L-Fuc-(1→4)]-α-L-Rha-OMe, an RG-II fragment that is linked to the apiosyl residue that is thought to be responsible for the borate complexation in RG-II dimer. Iterative glycosylation of the rhamnoside acceptors derived from the key 2,3-orthoacetate of methyl 4-O-methoxybenzyl- α-D-rhamnopyranoside afforded the protected tetrasaccharide. The target dicarboxylic acid saccharide was subsequently prepared by removal of protecting groups followed by TEMPO-mediated oxidation of galactopyranosyl residues to galactopyranosyluronic acids.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1605 |
| Faculty \ School: | Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 10 Sep 2024 12:30 |
| Last Modified: | 25 Sep 2024 18:08 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/96645 |
| DOI: | 10.1021/jo0482864 |
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