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PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
4
pubmed:dateCreated
2000-11-9
pubmed:abstractText
Pig organs transplanted into primates are rapidly rejected because of the interaction between Gal alpha(1-->3)Gal epitopes carried by the graft and natural antibodies (anti-alphaGal antibodies) present in the blood of the recipient. This report describes a simplified synthesis of the xenogeneic disaccharide and its linkage to activated gel matrices. The digalactosides alpha-D-Galp-(1-->3)-alpha,beta-D-Galp-OAll were synthesized by the condensation of the trichloroacetimidoyl 2,3,4,6-tetra-O-benzyl-beta-D-galactopyranoside donor with the 3,4-unprotected allyl 2,6-di-O-benzyl-alpha- or beta-D-galactopyranoside acceptor precursor. Deallylation and hydrogenolysis led to the free digalactoside, whereas hydrogenolysis alone resulted in the 1-O-propyl digalactoside. Both products were tested by inhibition ELISA of natural anti-Gal alpha(1-->3)Gal antibodies. The alpha-D-Galp-(1-->3)-beta-D-Galp-OPr was found to be the best inhibitor. Thus, the allyl group of the partially benzylated alpha-D-Galp-(1-->3)-beta-D-Galp-OAll was engineered, via the hydroxy-, the tosyloxy- and the azidopropyl intermediates, into an aminopropyl group amenable to binding to N-hydroxysuccinimide-activated agarose gel matrices in order to obtain specific immunoabsorption columns. Columns made of gel substituted with 5 micromol of disaccharide per milliliter were found efficient for the immunoabsorption of anti-alphaGal antibodies from human plasma.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
May
pubmed:issn
0008-6215
pubmed:author
pubmed:issnType
Print
pubmed:day
5
pubmed:volume
325
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
265-77
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed-meshheading:10839120-Carbohydrate Sequence, pubmed-meshheading:10839120-Chromatography, Affinity, pubmed-meshheading:10839120-Disaccharides, pubmed-meshheading:10839120-Dose-Response Relationship, Drug, pubmed-meshheading:10839120-Enzyme-Linked Immunosorbent Assay, pubmed-meshheading:10839120-Epitopes, pubmed-meshheading:10839120-Galactose, pubmed-meshheading:10839120-Humans, pubmed-meshheading:10839120-Immunoglobulin G, pubmed-meshheading:10839120-Immunoglobulin M, pubmed-meshheading:10839120-Immunosorbent Techniques, pubmed-meshheading:10839120-Models, Chemical, pubmed-meshheading:10839120-Molecular Sequence Data, pubmed-meshheading:10839120-Propylamines, pubmed-meshheading:10839120-Sepharose, pubmed-meshheading:10839120-Succinimides, pubmed-meshheading:10839120-Transplantation, Heterologous
pubmed:year
2000
pubmed:articleTitle
A novel synthesis of alpha-D-Galp-(1-->3)-beta-D-Galp-1-O-(CH2)3-NH2, its linkage to activated matrices and absorption of anti-alphaGal xenoantibodies by affinity columns.
pubmed:affiliation
Unité de Recherche sur l'Immunointervention dans les allo- et les xénotransplantations, INSERM Unité 437, Centre Hospitalier Universitaire de Nantes, France.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't