Chemo-enzymatic supported synthesis of the 3-sulfated Lewis a pentasaccharide on a multimeric polyethylene glycol.
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.
Malleron
Annie
A
Laboratoire de Chimie Organique Multifonctionnelle, Equipe Glycochimie Moléculaire et Macromoléculaire, Centre National de la Rercherche Scientifique, UMR 8182, Bâtiment 420, Universite Paris-Sud, Orsay, France.
Le Narvor
Christine
C
D002240:Carbohydrate Sequence; D002853:Chromatography, Liquid; D005647:Fucosyltransferases / Q000737:chemistry*; D006154:Guanosine Diphosphate Fucose / Q000737:chemistry; D007983:Lewis Blood Group Antigens; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008956:Models, Chemical; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry*; D011409:Propylene Glycols / Q000737:chemistry; D013461:Sulfur Oxides / Q000737:chemistry
D007983:Lewis Blood Group Antigens; D009844:Oligosaccharides; D011409:Propylene Glycols; D013461:Sulfur Oxides; C508367:benzyl O-(3-O-sulfogalactopyranosyl)-1-3-O-(fucopyranosyl-1-4)-O-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranoside; D006154:Guanosine Diphosphate Fucose; D011092:Polyethylene Glycols; C013084:lacto-N-neotetraose; D005647:Fucosyltransferases; C019818:3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase; C011118:sulfur trioxide; C008783:pentaerythritol