Treatment of benzyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside with 4-methoxybenzaldehyde dimethyl acetal in N,N-dimethylformamide in the presence of 4-toluenesulfonic acid afforded the 4,6-O-(4-methoxybenzylidene) acetal, which was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosy
Synthetic mucin fragments. Synthesis of a tetra- and two penta-saccharides containing the O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→3)-d-galactopyranose (“lacto-N-triose 1”) unit
✍ Scribed by Rakesh K. Jain; Katsunori Kohata; Saeed A. Abbas; Khushi L. Matta
- Publisher
- Elsevier Science
- Year
- 1988
- Tongue
- English
- Weight
- 460 KB
- Volume
- 182
- Category
- Article
- ISSN
- 0008-6215
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✦ Synopsis
We have previously" described the synthesis and use, as a glycosyl donor, of 0-(2,3,4,6-tctra-0-acetyi_P-D-galactopyracetyi-2-deoxy-~-D-glucopyranosyl)-(1~3)-2,4,6-tri-O-acctyi-~-D-galactopyranosyl bromide (1). Since then, bromide 1 has proved to be a useful and versatile glycosyl donor for the synthesis of a variety of mucin-type, higher oligosaccharide fragments. As an illustration of this use, we herein describe the synthesis of benzyl O-~-D-galactopyranosyl-(l~3)-0-(2-acetamido-2-deoxy-~-~-glucopyranosyl)-( l--+3)-AC0 5r 500 1 2 R, R = CHC&OMe-4 3 R' , R' GE cnC6n,0Me-4
📜 SIMILAR VOLUMES
Condensation of 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D- glucopyranosyl)-2,4,6-tri-O-acetyl-alpha-D-galactopyranosyl bromide (1) with benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-alpha-D-glucopyranoside in boiling benzene and in the presence of mercuric cyanide afforded a trisaccharide that
Recent years have seen a remarkable surge of interest in the study of U-Lfucosyltransferases. Of these L-fucosyltransferases, the enzyme (143)~a+fucosyltransferase has attracted a great deal of clinical interest as a potential tumor marker. This enzyme catalyzes the transfer of an L-fucosyl group f
Treatment of benzyl O-/?-n-galactopyranosyl-( 1+3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-j3-D-glucopyranoside with tert-butylchlorodiphenylsiiane afforded the 6'-0-tert-butyldiphenylsilyl ether, which was converted into the 3',4'-0-isopropylidene derivative. Methylation and subsequent removal of