Chemoenzymic synthesis of β-D-Gal(6-SO4)-(1→4)-D-GlcNAc, β-D-Gal-(1→4)-D-GlcNAc(6-SO4) and β-D-GlcNAc-(1→4)-D-GlcNAc(6-SO4) and their roles as fucosyl acceptors in reactions catalysed by human α-3-fucosyltransferases

Abstract

N-Acetyllactosamine 5 is obtained by transglycoslyation between p-nitrophenyl β-D-galactopyranoside 3 and N-acetyl-D-glucosamine 4 by using the β-galactosidase from Bacillus circulans as the biocatalyst. Sodium salts of β-Gal(6-SO₄)-(1→4)-GlcNAc 1 and β-Gal-(1→4)-GlcNAc(6-SO₄) 2 have been prepared from N-acetyllactosamine 5 in five and three steps respectively. β-D-GlcNAc-(1→4)-D-GlcNAc(6-SO₄) (di-N-acetylchitobiose 6-sulfate) 10 is synthesised from chitin in three steps. The products have been tested as fucosyl acceptors in reactions catalysed by recombinant human fucosyltransferases III to VII.