These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


Pubmed for Handhelds

PUBMED FOR HANDHELDS

Search MEDLINE/PubMed

  • Title: Synthetic mucin fragments. Benzyl O-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-(1----3)-O-beta-D- galactopyranosyl-(1----3)-O-[(2-acetamido-2-deoxy-beta-D-glucopyran osy l)- (1----6)]-2-acetamido-2-deoxy-alpha-D-galactopyranoside and benzyl O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta-D- galactopyranosyl-(1----3)-O-[beta-D-galactopyranosyl-(1----6)]-2-ac eta mido- 2-deoxy-alpha-D-galactopyranoside.
    Author: Thomas RL, Abbas SA, Matta KL.
    Journal: Carbohydr Res; 1988 Dec 01; 183(2):163-73. PubMed ID: 3214840.
    Abstract:
    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-galactopyranosyl bromide (1). Reductive ring-opening of the acetal group provided a 6-O-(4-methoxybenzyl) derivative (4) which was glycosylated with 1, followed by removal of the 4-methoxybenzyl ether group, to give benzyl 2-acetamido-2-deoxy-3,4-di-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyran osyl)- alpha-D-galactopyranoside (7). The disaccharide diol 5, obtained from 4, and benzyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl-(1----3) -O- (2,4,6-tri-O-acetyl-beta-D-galactopyranosyl)-(1----3)-2-acetamido-2-deox y- alpha-D-galactopyranoside (11) were similarly glycosylated with 1 to afford a trisaccharide derivative 9 and a tetrasaccharide derivative 14, respectively. Diol 11 was also condensed with 2-methyl-(3,4,6-tri-O-acetyl-1,2-di-deoxy-alpha-D-glucopyrano)-[2, 1-d]-2- oxazoline to give a tetrasaccharide derivative 16. O-Deacetylation of trisaccharides 7 and 9, and tetrasaccharides 14 and 16 furnished trisaccharides 8 and 10, and the title tetrasaccharides 15 and 17, respectively. The structures of compounds 8, 10, 15, and 17 were established by 13C-n.m.r. spectroscopy.
    [Abstract] [Full Text] [Related] [New Search]