A strategy for chemical synthesis of selectively methyl-esterified oligomers of galacturonic acid

Mads Hartvig Clausen, Malene Ryborg Jørgensen, Jesper Thorsen, Robert Madsen

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Abstract

The synthesis of monomethyl-esterified trigalacturonans 1-3 is described as part of a general strategy towards pectic oligosaccharides. The necessary monomeric building blocks were all prepared on a large scale from galactose pentaacetate. The glycosylations were carried out between galactose glycosyl donors and acceptors using the n-pentenyl glycosylation technique. Yields of the desired alpha-anomers were in the 50 to 74% range. The trigalactans thus obtained were then subjected to oxidation at C-6. Depending on the protecting group at this position the oxidation either produced the carboxylic acid or the corresponding methyl ester. Hereby, oligomers of galacturonic acid can be prepared with methyl esters introduced in a regiocontrolled fashion.
Original languageEnglish
JournalRoyal Chemical Society. Journal. Perkin Transactions 1
Volume1
Issue number5
Pages (from-to)543-551
ISSN1472-7781
Publication statusPublished - 2001

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