Synthesis of an octasaccharide fragment of high-mannose-type glycans of glycoproteins.
O-(alpha-D-Mannopyranosyl)-(1----2)-O-(alpha-D-mannopyranosyl)-(1----3)- O- [(alpha-D-mannopyranosyl)-(1----2)-O-(alpha-D-mannopyranosyl)-(1----6)]- O- (alpha-D-mannopyranosyl)-(1----6)-O-(beta-D-mannopyranosyl)-(1----4)-O-( 2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-2-deoxy- glucopyranose, an octasaccharide fragment of high-mannose type glycan of glycoproteins, was synthesized. Crucial glycosylation of trisaccharide intermediate, benzyl O-(2,4-di-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-(2-acetamido-3,6-di -O- benzyl-2-deoxy-beta-D-glucopyranosyl)-(1----4)-2-acetamido-3,6-di-O-benz yl-2- deoxy-beta-D-glucopyranoside, was successful only with a di-O-acetyltetradeca-O-benzyl-D-mannopentaosyl chloride. The use of the corresponding hexadeca-O-acetyl-D-mannopentaosyl bromide did not give the desired product.
Nukada
T
T
RIKEN (The Institute of Physical and Chemical Research), Saitama, Japan.
Kitajima
T
T
Nakahara
Y
Y
Ogawa
T
T
D000117:Acetylglucosamine / Q000737:chemistry*; D002240:Carbohydrate Sequence; D006023:Glycoproteins / Q000737:chemistry; D008358:Mannose / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis
D006023:Glycoproteins; D009844:Oligosaccharides; D011134:Polysaccharides; D014312:Trisaccharides; D008358:Mannose; D000117:Acetylglucosamine