Towards Keratan Sulfate – Chemoenzymatic Cascade Synthesis of Sulfated <i>N</i>‐Acetyllactosamine (LacNAc) Glycan Oligomers

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Abstract

<jats:title>Abstract</jats:title><jats:p>We report on a novel chemoenzymatic cascade for the synthesis of sulfated <jats:italic>N</jats:italic>‐acetyllactosamine [(3Galβ1,4GlcNAcβ1,)<jats:sub>n</jats:sub>, LacNAc] oligomer structures. Starting from a linker modified GlcNAc substrate di‐ and trisaccharides were first synthesized by sequential use of human β4‐galactosyltransferase‐1 (β4GalT‐1) and β3‐<jats:italic>N</jats:italic>‐acetylglucosaminyltransferase from <jats:italic>Helicobacter pylori</jats:italic> (β3GlcNAcT). Subsequent regioselective chemical sulfation rendered the C‐6 mono‐, di‐, and tri‐<jats:italic>O</jats:italic>‐sulfated products in good yields. Further enzymatic elongation by β4GalT‐1 and β3GlcNAcT in a sequential mode yielded 6‐<jats:italic>O</jats:italic>‐sulfated LacNAc oligomers up to hexasaccharide length with variable degrees of sulfation. These carbohydrate structures mimic the sulfation pattern found in keratan sulfate and are potential ligands for different classes of glycan binding proteins.</jats:p><jats:p><jats:boxed-text content-type="graphic" position="anchor"><jats:graphic xmlns:xlink="http://www.w3.org/1999/xlink" mimetype="image/gif" position="anchor" specific-use="enlarged-web-image" xlink:href="graphic/mcontent.gif"><jats:alt-text>magnified image</jats:alt-text></jats:graphic></jats:boxed-text></jats:p>

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