Rapid synthesis of self-assembling 1,2-thiomannobioside glycoconjugates as potential multivalent ligands of mannose-binding lectins Dedicated to Professor Sándor Antus on the occasion of his 70th birthday

Magdolna Csávás, Tamás Demeter, Mihály Herczeg, István Timári, Katalin E. Kövér, Pál Herczegh, Anikó Borbás

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Among the pathogen-associated carbohydrate patterns, the Man(α1→2)Man α disaccharide motif is of particular interest because its multivalent derivatives are considered as potential antiviral or antibacterial agents through interaction with mannose-binding lectins. We present a straightforward synthesis of amphiphilic compounds containing a hydrolytically stable S-linked 1,2-mannobioside residue, a tetraethylene glycol linker to ensure water solubility and various lipophilic carriers such as a hexadecyl chain and two pyrrolidinofullerene derivatives. According to a dynamic light scattering study, the obtained amphiphiles form nanoscale aggregates in water producing multivalent presentation of the thiomannobioside residue.

Original languageEnglish
Pages (from-to)6983-6986
Number of pages4
JournalTetrahedron Letters
Volume55
Issue number51
DOIs
Publication statusPublished - Dec 17 2014

Keywords

  • Amphiphilic
  • Ferrier glycoside
  • Glycomimetic
  • Multivalent
  • Photoinduced thiol-addition

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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