A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy.
A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building blocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.
Codée
Jeroen D C
JD
Leiden Institute of Chemistry, Gorlaeus Laboratories, Leiden University, PO Box 9502, 2300 RA Leiden, The Netherlands.
Stubba
Bas
B
Schiattarella
Marialuisa
M
Overkleeft
Herman S
HS
van Boeckel
Constant A A
CA
van Boom
Jacques H
JH
van der Marel
Gijsbert A
GA
D002240:Carbohydrate Sequence; D006031:Glycosylation; D006493:Heparin / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D014574:Uronic Acids / Q000138:chemical synthesis / Q000737:chemistry
D009844:Oligosaccharides; D014574:Uronic Acids; D006493:Heparin