Synthesis of apiose-containing oligosaccharide fragments of the plant cell wall: fragments of rhamnogalacturonan-II side chains A and B, and apiogalacturonan

Nepogodiev, Sergey A., Fais, Margherita, Hughes, David L. and Field, Robert A. (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

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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:	12 Oct 2025 11:30
URI:	https://ueaeprints.uea.ac.uk/id/eprint/38362
DOI:	10.1039/c1ob05587a

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