Synthesis of a sulfonic acid mimetic of the sulfated Lewis A pentasaccharide

Zsolt Jakab, Anikó Fekete, Magdolna Csávás, Anikó Borbás, András Lipták, Sándor Antus

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The first sulfonic acid mimetic of the sulfated Lewis A pentasaccharide in which the natural l-fucose unit is replaced by a d-arabinose ring was synthesized. Formation of the sulfonic acid moiety at a pentasaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the terminal d-galactose residue and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be obtained by double nucleophilic substitutions; efficient formation of the gulo-triflate derivatives required low-power microwave (MW) activation. Oxidation of the acetylthio group was carried out using Oxone in the presence of acetic acid.

Original languageEnglish
Pages (from-to)90-93
Number of pages4
JournalCarbohydrate Research
Volume350
DOIs
Publication statusPublished - Mar 1 2012

Keywords

  • Double nucleophilic displacement
  • Microwave activation
  • Selectins
  • Sialyl Lewis A
  • Sugar sulfonic acid
  • Sulfated Lewis A pentasaccharide

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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