Synthesis of the alpha-L-Araf-(1-->2)-beta-D-Galp-(1-->6)-beta-D-Galp-(1-->6)-[alpha-L-Araf-(1-->2)]-beta-D-Galp-(1-->6)-D-Gal hexasaccharide as a possible repeating unit of the cell-cultured exudates of Echinacea purpurea arabinogalactan.
For the characterization of the supposed epitope of an arabinogalactan, isolated from the extract of the cell-cultured Echinacea purpurea, the title hexasaccharide was synthesized. The whole synthetic route was based on the 6-O-(methoxydimethyl)methyl ether (MIP) protecting group strategy. 2-O-Benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta-D-galactopyranosyl-(1-->6)-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose was used to prepare the desired glycosyl donor and glycosyl acceptor both carrying a persistent O-benzyl group at position 2'. Reaction of the digalactose donor and the digalactose acceptor resulted in a beta-(1-->6)-linked galactose-containing tetrasaccharide in which OH-2' and OH-2"' were substituted with benzyl groups. Hydrogenolytic removal of the benzyl groups of the tetragalactose compound gave the diol aglycon which was diarabinosylated in one step to furnish the protected target compound, whose deprotection led to the title hexasaccharide. All of the synthesized compounds were characterized by 1H and 13C NMR spectra, as well as by MALDI-TOF mass-spectrometry measurements.
Csávás
M
M
Research Group for Carbohydrates of the Hungarian Academy of Sciences, PO Box 70, H-4010, Debrecen, Hungary.
Borbás
A
A
Jánossy
L
L
Batta
G
G
Lipták
A
A
D018929:Cell Culture Techniques / Q000379:methods; D020900:Echinacea / Q000737:chemistry*; D000939:Epitopes / Q000737:chemistry*; D005685:Galactans / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification*
D000939:Epitopes; D005685:Galactans; D009844:Oligosaccharides; D010936:Plant Extracts; C447501:alpha-L-Araf-(1-2)-beta-D-Galp-(1-6)-beta-D-Galp-(1-6)-(alpha-L-Araf-(1-2))-beta-D-Galp-(1-6)-D-Gal hexasaccharide; C005653:arabinogalactan