BIOMAT Database Logo BIOMAT Database Logo

Synthetic mucin fragments: benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-beta- D-glucopyranosyl)-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D- galactopyranoside and benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)- 3-O-[6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-beta-D- galactopyranosyl]-2-deoxy-alpha-D-galactopyranoside. 1984

C F Piskorz, and S A Abbas, and K L Matta

Glycosylation of benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-alpha-D- galactopyranoside with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide, catalyzed by mercuric cyanide, afforded benzyl-2-acetamido-4,6-O-benzylidene-2-deoxy-3- O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D- galactopyranoside (3). O-Deacetylation of 3 gave benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-beta- D-galactopyranosyl-alpha-D-galactopyranoside which, on acetalation with benzaldehyde-zinc chloride complex followed by acetylation of the resulting dibenzylidene acetal, gave the disaccharide diacetate (7). Cleavage of the acetal groups of 3 and 7 in hot, 80% aqueous acetic acid furnished, respectively, the disaccharide tetraacetate (4) and diacetate (8). O-Deacetylation of 8 in methanolic sodium methoxide gave the disaccharide (9). Condensation of 4 or 8 with 2-methyl-(3,4,6-tri-O-acetyl-1,2- dideoxy-alpha-D-glucopyrano)-[2,1-d]-2-oxazoline, followed by O-deacetylation, afforded the title tri- and tetra-saccharides, 12 and 14, respectively. The structures of compounds 9, 12, and 14 were established by 13C-n.m.r. spectroscopy.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D009077 Mucins High molecular weight mucoproteins that protect the surface of EPITHELIAL CELLS by providing a barrier to particulate matter and microorganisms. Membrane-anchored mucins may have additional roles concerned with protein interactions at the cell surface. Mucin
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009844 Oligosaccharides Carbohydrates consisting of between two (DISACCHARIDES) and ten MONOSACCHARIDES connected by either an alpha- or beta-glycosidic link. They are found throughout nature in both the free and bound form. Oligosaccharide
D009904 Optical Rotation The rotation of linearly polarized light as it passes through various media. Optical Activity,Activity, Optical,Rotation, Optical

Related Publications

C F Piskorz, and S A Abbas, and K L Matta
Synthetic mucin fragments: benzyl 2-acetamido-3-O-[3-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl) -beta-D-galactopyranosyl]-2-deoxy-alpha-D-galactopyranoside.
September 1984, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
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.
December 1988, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthetic mucin fragments. Benzyl O-beta-D-galactopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----6)-2-acetamido-2-deoxy-alpha-D-galactopyranoside and O-alpha-L-fucopyranosyl-(1----3)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----6)-2-acetamido-2-deoxy-D-galactopyranose.
June 1989, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthetic mucin fragments: methyl 3-O-(2-acetamido-2-deoxy-beta-D-galactopyranosyl-beta-D- 3-O-(2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl- beta-D-glucopyranosyl)-beta-D-galactoyranoside. pyranosyl)-beta-D-galactopyranoside.
September 1984, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthetic mucin fragments. Methyl 6-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-beta-D-galactopyranoside, methyl 3,4-di-O-(2-acetamido-2-deoxy- beta-D-glucopyranosyl)-beta-D-galactopyranoside, and methyl O-(2-acetamido-2- deoxy-beta-D-glucopyranosyl)-(1----3)-O-beta-D-galactopyranosyl-(1---- 3)-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-beta-D-galactopyr ano side.
March 1987, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthesis of benzyl 2-acetamido-3-O- and -6-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-2-deoxy-alpha -D-galactopyranoside.
February 1983, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthesis of benzyl O-(3-O-methyl-beta-D-galactopyranosyl)-(1-->3)-2- acetamido-2-deoxy-alpha-D-galactopyranoside and benzyl O-(beta-D- galactopyranosyl)-(1-->3)-2-acetamido-2-deoxy-6-O-methyl-alpha-D- galactopyranoside as specific acceptors for sialyltransferases.
July 1995, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthesis of 2-acetamido-2-deoxy-6-O-beta-D-galactopyranosyl-D-galactopyranose and o-nitrophenyl 2-acetamido-2-deoxy-6-O-beta-D-galactopyranosyl -alpha-D-galactopyranoside.
August 1984, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthesis of methyl O-(2-O-methyl-beta-D-galactopyranosyl)-(1----4)-O-(2- acetamido-2-deoxy-beta-D-glucopyranosyl)-(1----3)-beta-D- galactopyranoside and 4-nitrophenyl O-beta-D-galactopyranosyl-(1----4)-O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1----3)-beta-D-galactopyranoside.
August 1990, Carbohydrate research,
C F Piskorz, and S A Abbas, and K L Matta
Synthetic mucin fragments: 3-O-[2-acetamido-4,6-di-O-acetyl-2-deoxy-3-O -(2,3,4,6-tetra-O-acetyl-b-D-galactopyranosyl)-b-D-glucopyranosyl] -2,4,6-tri-O-acetyl-a-D-galactopyranosyl bromide and p-nitrophenyl 3-O-(2-acetamido-2-deoxy-3-O-b-D-galactopyranosyl-b-D glucopyranosyl)-b-D-galactopyranoside.
September 1984, Carbohydrate research,
Copied contents to your clipboard!