Synthesis of a 2,3,4-triglycosylated rhamnoside fragment of rhamnogalacturonan-II side chain a using a late stage oxidation approach

A.-L. Chauvin, S.A. Nepogodiev, R.A. Field

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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.
Original languageUndefined
Pages (from-to)960-966
Number of pages7
JournalJournal of Organic Chemistry
Issue number3
Publication statusPublished - 6 Jan 2005

Research Beacons, Institutes and Platforms

  • Manchester Institute of Biotechnology

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