6533b853fe1ef96bd12acd68
RESEARCH PRODUCT
Spacer-separated sialyl LewisX cyclopeptide conjugates as potential E-selectin ligands.
Holger HerznerHorst Kunzsubject
AzidesAnomerStereochemistryNeutrophilsOligosaccharidesConjugated systemLigandsBiochemistryPeptides CyclicAnalytical Chemistrychemistry.chemical_compoundMiceLewis Blood Group AntigensTetrasaccharideAnimalsProtecting groupSialyl Lewis X AntigenLigandOrganic ChemistryGlycopeptidesGeneral MedicinechemistryAmine gas treatingAzideE-SelectinConjugatedescription
Completely protected sialyl LewisX azide was synthesized from a neolactosamine azide precursor carrying a 3-O-allyloxycarbonyl group as the temporary protecting group. After its Pd(0)-catalyzed deprotection and stereoselective alpha-fucosylation, the obtained LewisX azide was subjected to O-deacetylation in the galactose unit and subsequent regio- and stereoselective sialylation. Reduction of the anomeric azido group afforded the sialyl LewisX amine building block. Two molecules of this tetrasaccharide ligand were conjugated to a preformed cyclooctapeptide containing two equidistant l-asparagine units equipped with carboxy-terminated tetraethyleneglycol side chains to give, after deprotection, the target glycopeptide conjugate. Preliminary biological evaluation of the synthesized bivalent sialyl LewisX cyclopeptide conjugate showed only slightly enhanced inhibition of E-selectin binding in spite of the given flexibility of the two linked saccharide determinants.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2006-09-01 | Carbohydrate research |