Total synthesis of 6-O-sulfo-sialylparagloboside: a widely useful glycoprobe for biochemical research.
The total synthesis of 6-O-sulfo-sialylparagloboside is described. A suitably protected beta-D-GlcpNAc-(1-->3)-beta-D-Galp-(1-->4)-D-GlcpOSE derivative was glycosylated with an alpha-D-Neup5Ac-(2-->3)-D-Galp derived imidate to give the corresponding protected alpha-D-Neup5Ac-(2-->3)-beta-D-Galp-(1-->4)-beta-d-GlcpNAc-(1-->3)-beta-D-Galp-(1-->4)-D-GlcpOSE pentasaccharide derivative. Proper manipulation of the protecting groups of the pentasaccharide afforded the corresponding glycosyl imidate, which was coupled with (2S,3R,4E)-2-azido-3-O-benzoyl-4-octadecene-1,3-diol. Selective reduction of the azido group, N-acylation with octadecanoic acid, 6-O-sulfation of the GlcpNAc residue, and complete removal of the protecting groups gave the desired 6-O-sulfo-sialylparagloboside.
Yamaguchi
Masanori
M
Department of Applied Bio-Organic Chemistry, Faculty of Applied Biological Sciences, Gifu University, Gifu, Japan. ymasanori0626@yahoo.co.jp
Ishida
Hideharu
H
Kiso
Makoto
M
D002240:Carbohydrate Sequence; D005915:Globosides / Q000138:chemical synthesis*; D006388:Hemagglutinins / Q000737:chemistry
C531227:6-O-sulfosialylparagloboside; D005915:Globosides; D006388:Hemagglutinins