59446-75-2

Upstream product

• 83259-21-6 O-(2-O-Acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1-> 3)-O-(6-O-acetyl-2,4-di-O-benzyl-β-D-mannopyranosyl)-(1-> 4)-1,6-anhydro-2-azido-3-O-benzyl-2-desoxy-β-D-glucopyranose 
• 77356-44-6 benzyl 2-acetamido-4-O-<2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranosyl>-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 133-89-1 UDP-glucose 
• 4307-58-8 N-acetyl-D-lactosamine 
• 7493-95-0 4-nitrophenyl α-D-galactoside 
• 57-50-1 sucrose 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 70267-71-9 2,3,4,6-tetra-O-benzyl-1-O-(N-methylacetimidoyl)-β-D-galactopyranose 
• 77396-73-7 benzyl 2-acetamido-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 77356-41-3 benzyl 2-acetamido-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 188302-08-1 C₆₁H₆₇NO₂₄ 
• 188302-09-2 C₅₅H₆₇NO₂₃ 
• 188302-05-8 Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-2-(4-acetylamino-phenoxy)-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl ester 
• 188302-07-0 Acetic acid (2R,3R,4S,5S,6R)-5-acetoxy-6-acetoxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Methods for synthesis of alpha-d-gal (1~>3) gal-containing oligosaccharides

This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising α-D-Gal(1→3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of α-D-galactopyranosyl-(1→3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R3 is methoxy or methyl; R1 is H, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl.

Chemo-enzymatic synthesis of the Galili epitope Galα(1→3)Galβ(1→4)GlcNAc on a homogeneously soluble PEG polymer by a multi-enzyme system

The α-Gal trisaccharide Galα(1→3)Galβ(1→4)GlcNAc 11 was synthesized on a homogeneously soluble polymeric support (polyethylene glycol, PEG) by use of a multi-enzyme system consisting of β-1,4-galactosyltransferase (EC 2.4.1.38), α-1,3-galactosyltransferase (EC 2.4.1.151), sucrose synthase (EC 2.4.1.13) and UDP-glucose-4-epimerase (EC 5.1.3.2). In addition workup was simplified by use of dia-ultrafiltration. Thus the advantages of classic chemistry/enzymology and solid-phase synthesis could be united in one. Subsequent hydrogenolytic cleavage afforded the free α-Gal trisaccharide.

Glycosidase-catalysed synthesis of α-galactosyl epitopes important in xenotransplantation and toxin binding using the α-galactosidase from Penicillium multicolor

The α-galactosidase from Penicillium multicolor catalyses highly regioselective galactosyl transfer on to mono- and di-saccharide accepters that have a non-reducing terminal galactose unit to give products containing the α-D-Galp-(1→3)-D-Galp epitope found on pig tissue and which is responsible for the hyperacute rejection response in xenotransplantation of pig organs into man.

Highly efficient chemoenzymatic synthesis of α-galactosyl epitopes with a recombinant α(1→3)-galactosyltransferase

α-Galactosyl epitopes are carbohydrate structures bearing a Galα1-3Galβ terminus. The interaction of these epitopes on the surface of animal cells with anti-α-galactosyl antibodies in human serum is believed to be the main cause in antibody-mediated hyper

Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc, and their PEG-conjugates

Galα1-3Gal-pNP was prepared enzymatically from Gal-pNP using α-galactosidase from coffee beans. PEG was attached after the reduction of nitro group into amino group to give Galα1-3Gal-PEG conjugate. After removing the pNP group in Galα1-3Gal-pNP, the obtained disaccharide was used for the synthesis of Galα1-3Galβ1-4GlcNAc and corresponding trisaccharide-PEG conjugate.

Synthesis of Blood-group Substances. Part 11. Synthesis of the Trisaccharide O-α-D-Galactopyranosyl-(1-->3)-O-β-D-galactopyranosyl-(1-->4)-2-acetamido-2-deoxy-D-glucopyranose

Reaction of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide with benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside in 1,2-dichloroethane in the presence of mercuric bromide and molecular sieves (4 Angstroem) provided after O-deacetylation

SYNTHESIS OF THE TETRASACCHARIDE O-α-L-FUCOPYRANOSYL-(1->2)-3)>-O-β-D-GALACTOPYRANOSYL-(1->4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE, THE ANTIGENIC DETERMINANT OF HUMAN BLOOD-GROUP B (TYPE 2)

Treatment of benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside with benzaldehyde in the presence of zinc chloride, followed by regioselective benzoylation (N-benzoylimidazole in dichloromethane) provided crystalline benzyl 2-acetamido-4-O-(3-O-benzoyl-4,6-O-benzylidene-β-D-galactopyranosyl)-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside.Condensation of this disaccharide with 2,3,4-tri-O-benzyl-1-O-(N-methylacetimidyl)-β-L-fucopyranose in nitromethane in the presence of p-toluenesulfonic acid and molecular sieves 4 Angstroem gave benzyl O-(2,3,4,-tri-O-benzyl-α-L-fucopyranosyl)-(1->2)-O-(3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranosyl)-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside.Debenzoylation, followed by condensation with 2,3,4,6-tetra-O-benzyl-1-O-(N-methylacetimidyl)-β-D-galactopyranose under the same conditions provided a tetrasaccharide derivative that was catalytically hydrogenolyzed into the title compound.