449177-38-2Relevant academic research and scientific papers
Synthesis of the trifucosylated N-linked hexasaccharide of a glycoprotein from Haemonchus contortus
Soederman, Peter,Larsson, E. Andreas,Widmalm, Goeran
, p. 1614 - 1618 (2007/10/03)
The synthesis of a hexasaccharide from the inner part of an N-linked oligosaccharide portion of a glycoprotein from Haemonchus contortus is described. This hexasaccharide contains a novel fucosylation pattern with three α-linked fucosyl groups at 0-3, 0-6 and 0-3′ of the two N-acetylglucosamine residues. In the synthesis two consecutive regioselective glycosylations were performed, thereby limiting protecting group manipulations, to yield a trisaccharide with β-(1→4) linkages. Subsequent trifucosylation in one step, followed by inversion of configuration via a displacement reaction at C-2″ of the terminal glucosyl residue produced the resulting β-mannosyl linkage. The 2-acetamido-2-deoxy-glucosylamine residue was capped by an N-acetyl group and the hexasaccharide was deprotected. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
