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  • Chemo-enzymatic supported synthesis of the 3-sulfated Lewis a pentasaccharide on a multimeric polyethylene glycol.

Chemo-enzymatic supported synthesis of the 3-sulfated Lewis a pentasaccharide on a multimeric polyethylene glycol.

Carbohydrate research (2008-02-19)
Annie Malleron, Christine Le Narvor
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.

MATERIALS
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Sigma-Aldrich
Pentaerythritol, 99%
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Sigma-Aldrich
Pentaerythritol, 98%
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Sigma-Aldrich
Guanosine 5′-diphospho-β-L-fucose sodium salt, ≥85%
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