Chemoenzymatic synthesis of a 3IV,6III-disulfated Lewis(x) pentasaccharide, a candidate ligand for human L-selectin

Carbohydrate Research
A LubineauC Le Narvor

Abstract

The disulfated pentasaccharide 3-O-SO3(-)-beta-D-Galp-(1-->4)-[alpha-L-Fucp-(1-->3)]-6-O-SO3(-)- beta-D-GlcpNAc-(1-->3)-beta-D-Galp-(1-->4)-D-Glcp was prepared according to a chemoenzymatic approach, starting from 4-methoxybenzyl O-(4-O-acetyl-2,6-di-O-benzyl-beta- D-galactopyranosyl)-(1-->4)-O-2,3,6-tri-O-benzyl-beta-D-glucopyranoside, obtained in six steps from hepta-O-acetyl lactosyl bromide. Coupling of this lactose derivative with O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl) trichloracetimidate afforded, after dephthaloylation and re-N-acetylation, 4-methoxybenzyl O-(2-acetamido-2-deoxy-beta-D- glucopyranosyl)-(1-->3)-O-(2,6-di-O-benzyl-beta-D-galactopyranosyl)-(1-- >4)- O-2,3,6-tri-O-benzyl-beta-D-glucopyranoside. Regioselective sulfation at the primary position of the glucosamine residue was then successfully achieved and the benzyl groups were removed. Enzymatic galactosylation of 4-methoxybenzyl O-(2-acetamido-2-deoxy-6-O-sulfo-beta-D- glucopyranosyl)-(1-->3)-O-beta-D-galactopyranosyl-(1-->4)-O-beta-D- glucopyranoside sodium salt, and subsequent regioselective sulfation at position 3 of the outer galactose residue through the stannylene procedure, led then to 4-methoxybenzyl O-(3-sulfo-beta-D- gal...Continue Reading

References

May 19, 1995·The Journal of Biological Chemistry·S HemmerichS D Rosen
Sep 15, 1993·European Journal of Biochemistry·T de VriesD H Van den Eijnden
Apr 26, 1994·Biochemistry·S Hemmerich, S D Rosen
Aug 15, 1995·Physical Review. D·D Lemoine, M Lemoine

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Citations

Dec 22, 1999·Current Opinion in Biotechnology·M M Palcic
Jan 17, 2002·Bioscience, Biotechnology, and Biochemistry·T MurataT Usui
Jul 10, 2003·Chembiochem : a European Journal of Chemical Biology·Hirotaka UzawaKazukiyo Kobayashi
Mar 4, 2003·Chemical Communications : Chem Comm·Hirotaka UzawaNorihiko Minoura
Nov 9, 2005·Carbohydrate Research·Annie MalleronChristine Le Narvor

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