Stereoselective synthesis of a sulfated tetrasaccharide corresponding to a rare sequence in the galactofucan isolated from Sargassum polycystum.
The first chemical synthesis of a highly sulfated tetrasaccharide 1, as the rare sequence in the galactofucan isolated from the brown alga Sargassum polycystum, was achieved in a convergent and stereoselective manner. The key features of the synthetic strategy include construction of multiple contiguous 1,2-cis glycosidic bonds and [2 + 2] assembly based on the rationally developed d-galactose building block 6. The synthesized oligosaccharides were fully characterized using a combination of coupled-HSQC and other 2D NMR techniques.
Shanghai Engineering Research Centre of Molecular Therapeutics and New Drug Development, and Department of Chemistry, East China Normal University , Shanghai, 200062, PR China.
Jun
J
Zhou
Liping
L
Yang
Wenhao
W
Hu
D005643:Fucose / Q000737:chemistry*; D005690:Galactose / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D044647:Sargassum / Q000737:chemistry*; D013431:Sulfates / Q000737:chemistry*
D009844:Oligosaccharides; D013431:Sulfates; D005643:Fucose; D005690:Galactose