- Methods for synthesis of alpha-d-gal (1~>3) gal-containing oligosaccharides
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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.
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- 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
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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.
- Brinkmann, Nils,Malissard, Martine,Ramuz, Maud,Roemer, Ulrike,Schumacher, Thomas,Berger, Eric G.,Elling, Lothar,Wandrey, Christian,Liese, Andreas
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p. 2503 - 2506
(2007/10/03)
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- Glycosidase-catalysed synthesis of α-galactosyl epitopes important in xenotransplantation and toxin binding using the α-galactosidase from Penicillium multicolor
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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.
- Singh, Suddham,Scigelova, Michaela,Crout, David H. G.
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p. 2065 - 2066
(2007/10/03)
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- Highly efficient chemoenzymatic synthesis of α-galactosyl epitopes with a recombinant α(1→3)-galactosyltransferase
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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
- Fang, Jianwen,Li, Jun,Chen, Xi,Zhang, Yingnan,Wang, Jianqiang,Guo, Zhengmao,Zhang, Wei,Yu, Libing,Brew, Keith,Wang, Peng George
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p. 6635 - 6638
(2007/10/03)
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- Chemoenzymatic synthesis of Galα1-3Gal, Galα1-3Galβ1-4GlcNAc, and their PEG-conjugates
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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.
- Matsuo, Ichiro,Fujimoto, Hiroshi,Isomura, Megumi,Ajisaka, Katsumi
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p. 255 - 258
(2007/10/03)
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- 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)
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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.
- Milat, Marie-Louise,Sinay, Pierre
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p. 183 - 190
(2007/10/02)
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- 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
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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
- Jacquinet, Jean-Claude,Duchet, Danielle,Milat, Marie-Louise,Sinay, Pierre
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p. 326 - 330
(2007/10/02)
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