Multivalent sialylation of beta-thio-glycoclusters by Trypanosoma cruzi trans sialidase and analysis by high performance anion exchange chromatography - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Glycoconjugate Journal Année : 2016

Multivalent sialylation of beta-thio-glycoclusters by Trypanosoma cruzi trans sialidase and analysis by high performance anion exchange chromatography

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Rosalia Agusti
  • Fonction : Auteur
Maria Emilia Cano
  • Fonction : Auteur
Alejandro J. Cagnoni
  • Fonction : Auteur
Rosa M. De Lederkremer
  • Fonction : Auteur
Maria Laura Uhrig
  • Fonction : Auteur

Résumé

The synthesis of multivalent sialylated glycoclusters is herein addressed by a chemoenzymatic approach using the trans-sialidase of Trypanosoma cruzi (TcTS). Multivalent beta-thio-galactopyranosides and beta-thio-lactosides were used as acceptor substrates and 3'-sialyllactose as the sialic acid donor. High performance anion exchange chromatography with pulsed amperometric detection (HPAEC-PAD) was shown to be an excellent technique for the analysis of the reaction products. Different eluting conditions were optimized to allow the simultaneous resolution of the sialylated species, as well as their neutral precursors. The TcTS efficiently transferred sialyl residues to di, tri, tetra and octa beta-thio-galactosides. In the case of an octavalent thiolactoside, up to six polysialylated compounds could be resolved. Preparative sialylation reactions were performed using the tetravalent and octavalent acceptor substrates. The main sialylated derivatives could be unequivocally assigned by MALDI mass spectrometry. Inhibition of the transfer to the natural substrate, N-acetyllactosamine, was also studied. The octalactoside caused 82 % inhibition of sialic acid transfer when we used equimolar concentrations of donor, acceptor and inhibitor.

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Dates et versions

hal-03613825 , version 1 (18-03-2022)

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Rosalia Agusti, Maria Emilia Cano, Alejandro J. Cagnoni, Jose Kovensky, Rosa M. De Lederkremer, et al.. Multivalent sialylation of beta-thio-glycoclusters by Trypanosoma cruzi trans sialidase and analysis by high performance anion exchange chromatography. Glycoconjugate Journal, 2016, 33 (5), pp.809-818. ⟨10.1007/s10719-016-9676-0⟩. ⟨hal-03613825⟩
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