Synthesis of a sulfonic acid mimetic of the sulfated Lewis A pentasaccharide.
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.
Research Group for Carbohydrates of the Hungarian Academy of Sciences, University of Debrecen, Pusztaszeri út 59-67, Debrecen, Hungary.
Zsolt
Z
Jakab
Anikó
A
Fekete
Magdolna
M
Csávás
Anikó
A
Borbás
András
A
Lipták
Sándor
S
Antus
D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D058116:Lewis Acids / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry*; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000737:chemistry
D058116:Lewis Acids; D009844:Oligosaccharides; D013431:Sulfates; D013451:Sulfonic Acids