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

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

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)


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.
Original languageEnglish
Pages (from-to)6670-6684
Number of pages15
JournalOrganic & Biomolecular Chemistry
Issue number19
Publication statusPublished - 20 Jun 2011

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