Total synthesis of sialylated and sulfated oligosaccharide chains from respiratory mucins

Autor: J, Xia, J L, Alderfer, C F, Piskorz, K L, Matta
Rok vydání: 2000
Předmět:
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany). 6(18)
ISSN: 0947-6539
Popis: The total syntheses of several complex oligosaccharide moieties that occur in the core structure of sulfated mucins are reported. A trisaccharide acceptor was obtained through regio- and stereoselective sialylation of methyl (6-O-pivaloyl-beta-D-galactopyanosyl)(1--3)-4,6-O-benzylidene-2-a cetamido-2-deoxy-alpha-D-galactopyranoside with a novel sialyl donor. A tetrasaccharide, pentasaccharide, and hexasaccharide were constructed in predictable and controlled manner with high regio- and stereoselectivity after the successful preparation and employment of a disaccharide donor, trisaccharide donor, disaccharide acceptor, and trisaccharide acceptor building blocks. Finally, a mild oxidative cleaving method was adopted for the selective removal of 2-naphthylmethyl (NAP) in the presence of benzyl groups.
Databáze: OpenAIRE