314075-31-5Relevant articles and documents
New derivatives of reducing oligosaccharides and their use in enzymatic reactions: Efficient synthesis of sialyl Lewis a and sialyl dimeric Lewis x glycoconjugates
Barstroem, Mattias,Bengtsson, Mia,Blixt, Ola,Norberg, Thomas
, p. 525 - 531 (2007/10/03)
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-deoxyalditol 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. (C) 2000 Elsevier Science Ltd.