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

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 glycos...

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Published inPerkin 1 : an international journal of organic and bio-organic chemistry no. 5; pp. 543 - 551
Main Authors Clausen, MH, Jorgensen, MR, Thorsen, J, Madsen, R
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASPERGILLUS-NIGER
CELL-WALL GLYCANS
ERWINIA-CHRYSANTHEMI-3937
PERFORMANCE
PENTENYL GLYCOSIDES
CHEMISTRY
PHYTOALEXIN ELICITOR
ENDOPOLYGALACTURONASE
EFFICIENT
MASS-SPECTROMETRY
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Summary: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.
ISSN:1472-7781
DOI:10.1039/b006981g