Linked Life Data

19665108

Source:http://linkedlifedata.com/resource/pubmed/id/19665108

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
13
pubmed:dateCreated
2009-8-28
pubmed:abstractText
In order to define binding interactions of Kdo-specific monoclonal antibodies directed against the chlamydial alpha-(2-->8)-linked Kdo disaccharide epitope on a molecular level, modifications at the 7-position of the proximal and distal Kdo unit were investigated. The synthesis of 7-O-methyl and 7-azido-7-deoxy-7-epi-Kdo monosaccharide derivatives was achieved via an 8-O-TBS protected derivative, whereas methylation of O-7 at the proximal Kdo unit of the alpha-(2-->8)-linked Kdo disaccharide was conveniently accomplished via a 4,5; 4',5'; 7',8'-tri-O-carbonyl-protected disaccharide intermediate. Attempted epimerization at C-5 of the inner unit of a alpha-(2-->4)-linked Kdo disaccharide, however, resulted in formation of the corresponding 5,6-dehydro derivative, which was fully deprotected. Treatment of unprotected alpha-(2-->8)- as well as alpha-(2-->4)-linked Kdo disaccharides in neat acetic acid furnished the corresponding interresidue lactone derivatives. The lactones displayed limited stability under neutral conditions and were hydrolyzed at pH 7 within 3 days. Access to the lactones, however, provides a means for selective derivatization of the carboxylic group located at the distal Kdo residue, which was demonstrated by methanolysis of the lactone to afford the monomethyl ester of the alpha-(2-->8)-linked Kdo disaccharide. ELISA inhibition experiments of the ligands with two Kdo-specific monoclonal antibodies showed slightly reduced reactivity for the binding of the alpha-(2-->8) Kdo-specific antibody S25-2, whereas the 7-O-methyl disaccharide antigen displayed high binding affinity toward the Kdo monosaccharide-specific antibody S67-27.
pubmed:grant
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Sep
pubmed:issn
1873-426X
pubmed:author
pubmed:issnType
Electronic
pubmed:day
8
pubmed:volume
344
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
1660-9
pubmed:dateRevised
2011-4-6
pubmed:meshHeading
pubmed:year
2009
pubmed:articleTitle
Synthesis and antigenic properties of C-7-modified Kdo mono- and disaccharide ligands and Kdo disaccharide interresidue lactones.
pubmed:affiliation
Department of Chemistry, University of Natural Resources and Applied Life Sciences, Muthgasse 18, A-1190 Vienna, Austria.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't