Chemoenzymatic synthesis of the 3-sulfated Lewisa pentasaccharide |
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Authors: | Malleron Annie Hersant Yaël Le Narvor Christine |
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Affiliation: | Laboratoire de Chimie Organique Multifonctionnelle, UMR 8614, GDR 2590, Bat. 420, Université de Paris Sud, F-91405 Orsay, France. |
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Abstract: | 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. |
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Keywords: | Chemo-enzymatic synthesis Fucosyltransferase Sulfated Lewisa pentasaccharide |
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