Synthesis of new sulfonic acid-containing oligosaccharide mimetics of sialyl Lewis A

Zsolt Jakab, Anikó Fekete, A. Borbás, A. Lipták, S. Antus

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Two trisaccharides as new sulfonic acid mimetics of the sialyl Lewis A tetrasaccharide were synthesized. The natural sialic acid residue is replaced by a C-sulfonic acid moiety attached to position C-3′ of the lactosamine unit of the mimetics. The l-fucose unit was also replaced by a d-arabinose ring in one of the analogues. Formation of the sulfonic acid moiety on the trisaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the galactose skeleton and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be achieved by double nucleophilic substitution; efficient formation of the gulo-triflate derivatives required low-power microwave activation. Oxidation of the acetylthio group was carried out using Oxone in acetic acid.

Original languageEnglish
Pages (from-to)2404-2414
Number of pages11
JournalTetrahedron
Volume66
Issue number13
DOIs
Publication statusPublished - Mar 27 2010

Fingerprint

Sulfonic Acids
Oligosaccharides
Trisaccharides
Galactose
Mustelidae
Oxidation
Arabinose
Fucose
N-Acetylneuraminic Acid
Microwaves
Skeleton
Acetic Acid
Substitution reactions
Chemical activation
Derivatives

Keywords

  • Double nucleophilic displacement
  • Selectins
  • Sialyl Lewis A
  • Sugar sulfonic acid

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of new sulfonic acid-containing oligosaccharide mimetics of sialyl Lewis A. / Jakab, Zsolt; Fekete, Anikó; Borbás, A.; Lipták, A.; Antus, S.

In: Tetrahedron, Vol. 66, No. 13, 27.03.2010, p. 2404-2414.

Research output: Contribution to journalArticle

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AU - Borbás, A.

AU - Lipták, A.

AU - Antus, S.

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AB - Two trisaccharides as new sulfonic acid mimetics of the sialyl Lewis A tetrasaccharide were synthesized. The natural sialic acid residue is replaced by a C-sulfonic acid moiety attached to position C-3′ of the lactosamine unit of the mimetics. The l-fucose unit was also replaced by a d-arabinose ring in one of the analogues. Formation of the sulfonic acid moiety on the trisaccharide level could be successfully achieved by means of introduction of an acetylthio moiety into the galactose skeleton and subsequent oxidation. The equatorial arrangement of the acetylthio group linked to C-3 of the galactose ring could be achieved by double nucleophilic substitution; efficient formation of the gulo-triflate derivatives required low-power microwave activation. Oxidation of the acetylthio group was carried out using Oxone in acetic acid.

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