Abstract
The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->3)-4,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate with (2,6-di-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-(2,3,6-tri-O-acetyl-beta-D-glucopyranoside) bound onto the polymer afforded lacto-N-tetraose, which was then regioselectively sulfated at the 3-OH position of the terminal galactose using the stannylene procedure. Fucosylation of the sulfated tetrasaccharide was performed using an immobilized fucosyltransferase FucTIII to give the title compound after cleavage.
MeSH terms
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Carbohydrate Sequence
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Chromatography, Liquid
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Fucosyltransferases / chemistry*
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Guanosine Diphosphate Fucose / chemistry
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Lewis Blood Group Antigens
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Models, Chemical
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Molecular Sequence Data
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Molecular Structure
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Oligosaccharides / chemical synthesis*
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Oligosaccharides / chemistry
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Polyethylene Glycols / chemistry*
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Propylene Glycols / chemistry
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Sulfur Oxides / chemistry
Substances
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Lewis Blood Group Antigens
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Oligosaccharides
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Propylene Glycols
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Sulfur Oxides
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benzyl O-(3-O-sulfogalactopyranosyl)-1-3-O-(fucopyranosyl-1-4)-O-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranoside
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Guanosine Diphosphate Fucose
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Polyethylene Glycols
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lacto-N-neotetraose
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Fucosyltransferases
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3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase
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sulfur trioxide
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pentaerythritol