Chemoenzymatic synthesis of the 3-sulfated Lewisa pentasaccharide.
The sulfated pentasaccharide benzyl O-(3-O-sulfo-beta-D-galactopyranosyl)-(1-->3)-O-[(alpha-L-fucopyranosyl)-(1-->4)]-O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->3)-O-(beta-D-galactopyranosyl)-(1-->4)-O-beta-D-glucopyranoside sodium salt was synthesized using a chemo-enzymatic approach. Lacto-N-tetraose, obtained from two disaccharides [4-methoxybenzyl O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->3)-4,6-O-benzylidene-2-deoxy-2-phtalimido-beta-D-glucopyranoside and benzyl 2,6-di-O-acetyl-beta-D-galactopyranosyl-(1-->4)-2,3,6-tri-O-acetyl-beta-D-glucopyranoside], was regioselectively sulfated at the 3 OH position of the terminal galactose using the stannylene procedure. The fucosylation of the sulfated tetrasaccharide was performed using soluble or immobilized fucosyltransferase FucT-III to give the title compound.
Malleron
Annie
A
Laboratoire de Chimie Organique Multifonctionnelle, UMR 8614, GDR 2590, Bât. 420, Université de Paris Sud, F-91405 Orsay, France.
Hersant
Yaël
Y
Le Narvor
Christine
C
D002240:Carbohydrate Sequence; D005647:Fucosyltransferases / Q000378:metabolism; D007983:Lewis Blood Group Antigens; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013463:Sulfuric Acid Esters / Q000138:chemical synthesis
D007983:Lewis Blood Group Antigens; D009844:Oligosaccharides; D013463:Sulfuric Acid Esters; C508367:benzyl O-(3-O-sulfogalactopyranosyl)-1-3-O-(fucopyranosyl-1-4)-O-(2-acetamido-2-deoxyglucopyranosyl)-1-3-galactopyranosyl-1-4-glucopyranoside; D005647:Fucosyltransferases; C019818:3-galactosyl-N-acetylglucosaminide 4-alpha-L-fucosyltransferase