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RESEARCH PRODUCT
Chemoenzymatic Synthesis of Functional Sialyl LewisX Mimetics with a Heteroaromatic Core
Patrick ZiegelmüllerTill OpatzChristine WiebeDanuta KowalczykClaudine SchlemmerDorota FerencStefanie WedepohlJens Derneddesubject
Spectrometry Mass Electrospray IonizationStereochemistryProton Magnetic Resonance SpectroscopyTrypanosoma cruziMolecular Sequence DataNeuraminidaseOligosaccharidessaccharide mimeticsBiochemistryenzyme catalysisEnzyme catalysischemistry.chemical_compoundSulfationTetrasaccharideAnimalsGlycosylTyrosineCarbon-13 Magnetic Resonance SpectroscopySialyl Lewis X AntigenGlycoproteinsIndole testheterocyclesOrganic ChemistryMolecular Mimicrycell adhesionGeneral ChemistryFull Paperscarbohydrates (lipids)Sialyl-Lewis XchemistryCarbohydrate SequenceSelectinsAzidedescription
Functional mimetics of the sialyl Lewis(X) tetrasaccharide were prepared by the enzymatic sialylation of a 1,3-diglycosylated indole and a glycosyl azide, which was subsequently transformed into a 1,4-diglycosylated 1,2,3-triazole, by using the trans-sialidase of Trypanosoma cruzi. These compounds inhibited the binding of E-, L-, and P-selectin-coated nanoparticles to polyacrylamide-bound sialyl-Lewis(X) -containing neighboring sulfated tyrosine residues (sTyr/sLe(X) -PAA) at low or sub-millimolar concentrations. Except for E-selectin, the mimetics showed higher activities than the natural tetrasaccharide.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2014-05-01 | Chemistry, an Asian Journal |