Synthesis of oligosaccharides with oligoethylene glycol spacers and their conversion into glycoconjugates using N,N,N',N'-tetramethyl(succinimido)uronium tetrafluoroborate as coupling reagent.
Glycosides of glucose and lactose with di- and tetraethylene glycols, transformed into bifunctional (alcohol, ester) spacer molecules, have been synthesized. After deprotection, these spacer glycosides, containing a free carboxyl group, have been transformed efficiently into glycoconjugates using N,N,N',N'-tetramethyl(succinimido)uronium tetrafluoroborate (TSTU) for the formation of an active ester.
Andersson
M
M
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Oscarson
S
S
Ohberg
L
L
D005026:Ethylene Glycols / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D007202:Indicators and Reagents; D008782:Methylurea Compounds; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013388:Succinimides
D005026:Ethylene Glycols; D006001:Glycoconjugates; D007202:Indicators and Reagents; D008782:Methylurea Compounds; C087069:N,N,N',N'-tetramethyl(succinimido)uronium tetrafluoroborate; D009844:Oligosaccharides; D013388:Succinimides