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rdf:type | |
lifeskim:mentions | |
pubmed:dateCreated |
1993-4-28
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pubmed:abstractText |
D-Galacturonic acid or (1-->4)-alpha-D-galacturonan reacted in aqueous pyridine in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide with alcohols to yield esters. The alcohols that gave high yields of D-galacturonoyl derivatives were primary and included methanol, ethanol, 1-propanol, D-glucose, D-galactose, methyl beta-D-glucopyranoside, methyl beta-D-galactopyranoside, and cellulose. D-Galacturonic acid itself readily gave an O-D-galacturonoyl-D-glacturonic acid. The proposed structure of one compound, methyl 6-O-D-galacturonoyl-beta-D-glucopyranoside, was supported by 1H and 13C NMR data and the FAB mass-spectral data. Each ester was hydrolysed at pH 11 and 25 degrees C within 1 h. O-D-Galacturonoyl-D-glucose was considerably more alkali labile than O-polygalacturonoyl-D-glucose, and O-D-galacturonoylcellulose had an intermediate stability. The esters were relatively stable to cold acid, but could be hydrolysed by M trifluoroacetic acid at 100 degrees C for 1 h. The esters tested were resistant to digestion by 'Driselase', although the glycosidic bonds of O-polygalacturonoyl-D-glucose were hydrolysed to yield O-oligogalacturonoyl-D-glucoses of low molecular weight. The possible application of these analytical methods to the detection of O-uronoyl-type cross-links in cell-wall polysaccharides is discussed.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Disaccharides,
http://linkedlifedata.com/resource/pubmed/chemical/Esters,
http://linkedlifedata.com/resource/pubmed/chemical/Galactosides,
http://linkedlifedata.com/resource/pubmed/chemical/Glucosides,
http://linkedlifedata.com/resource/pubmed/chemical/Hexuronic Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Pectins,
http://linkedlifedata.com/resource/pubmed/chemical/Polysaccharides,
http://linkedlifedata.com/resource/pubmed/chemical/Xylans,
http://linkedlifedata.com/resource/pubmed/chemical/galacturonic acid,
http://linkedlifedata.com/resource/pubmed/chemical/pectin
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pubmed:status |
MEDLINE
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pubmed:month |
Feb
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pubmed:issn |
0008-6215
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:day |
24
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pubmed:volume |
240
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
95-106
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pubmed:dateRevised |
2006-11-15
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pubmed:meshHeading |
pubmed-meshheading:8458018-Carbohydrate Sequence,
pubmed-meshheading:8458018-Cell Wall,
pubmed-meshheading:8458018-Disaccharides,
pubmed-meshheading:8458018-Esters,
pubmed-meshheading:8458018-Galactosides,
pubmed-meshheading:8458018-Glucosides,
pubmed-meshheading:8458018-Hexuronic Acids,
pubmed-meshheading:8458018-Hydrolysis,
pubmed-meshheading:8458018-Molecular Sequence Data,
pubmed-meshheading:8458018-Pectins,
pubmed-meshheading:8458018-Polysaccharides,
pubmed-meshheading:8458018-Xylans
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pubmed:year |
1993
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pubmed:articleTitle |
The preparation and susceptibility to hydrolysis of novel O-galacturonoyl derivatives of carbohydrates.
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pubmed:affiliation |
Division of Biological Sciences, University of Edinburgh, United Kingdom.
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pubmed:publicationType |
Journal Article,
Research Support, U.S. Gov't, Non-P.H.S.,
Research Support, Non-U.S. Gov't
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