New derivatives of reducing oligosaccharides and their use in enzymatic reactions: efficient synthesis of sialyl Lewis a and sialyl dimeric Lewis x glycoconjugates.
The reducing oligosaccharides lactose and lacto-N-tetraose were reductively aminated with benzyloxycarbonylaminoaniline and sodium cyanoborohydride, followed by treatment of the resulting secondary amines with acetic anhydride. The resulting N-acetyl-N-(4-benzyloxycarbonylaminophenyl)-1-amino-1-deoxyaldi tol oligosaccharide derivatives were subjected to stepwise enzymatic elongation with various glycosyltransferases/nucleotide sugars. Purification of the products after each enzymatic step was conveniently performed by solid-phase extraction on silica gel C-18 cartridges. Two oligosaccharide derivatives (with sialyl Lewis a and sialyl dimeric Lewis x structures) were prepared. Conversion of the obtained derivatives into neoglycoproteins by the sequence hydrogenolysis, thiophosgene treatment, and protein coupling was carried out.
Bårström
M
M
Department of Chemistry, Swedish University of Agricultural Sciences, Uppsala.
Bengtsson
M
M
Blixt
O
O
Norberg
T
T
D002240:Carbohydrate Sequence; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry; D016695:Glycosyltransferases / Q000737:chemistry / Q000378:metabolism*; D006801:Humans; D016256:Lewis X Antigen / Q000737:chemistry; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D000080506:Sialyl Lewis X Antigen
D006001:Glycoconjugates; D016256:Lewis X Antigen; D009844:Oligosaccharides; D000080506:Sialyl Lewis X Antigen; C069719:sialosyl dimeric Le(x) antigen; D016695:Glycosyltransferases