Towards Keratan Sulfate - Chemoenzymatic Cascade Synthesis of Sulfated N-Acetyllactosamine (LacNAc) Glycan Oligomers

0460034 - MBÚ 2017 RIV DE eng J - Journal Article
Lange, B. - Šimonová, Anna - Fischoeder, T. - Pelantová, Helena - Křen, Vladimír - Elling, L.
Towards Keratan Sulfate - Chemoenzymatic Cascade Synthesis of Sulfated N-Acetyllactosamine (LacNAc) Glycan Oligomers.
Advanced Synthesis & Catalysis. Roč. 358, č. 4 (2016), s. 584-596. ISSN 1615-4150. E-ISSN 1615-4169
R&D Projects: GA MŠMT(CZ) LD13042; GA ČR GC15-02578J
Institutional support: RVO:61388971
Keywords : biocatalysis * carbohydrates * glycoconjugates
Subject RIV: CE - Biochemistry
Impact factor: 5.646, year: 2016

We report on a novel chemoenzymatic cascade for the synthesis of sulfated N-acetyllactosamine [(3Gal1,4GlcNAc1,)(n), LacNAc] oligomer structures. Starting from a linker modified GlcNAc substrate di- and trisaccharides were first synthesized by sequential use of human 4-galactosyltransferase-1 (4GalT-1) and 3-N-acetylglucosaminyltransferase from Helicobacter pylori (3GlcNAcT). Subsequent regioselective chemical sulfation rendered the C-6 mono-, di-, and tri-O-sulfated products in good yields. Further enzymatic elongation by 4GalT-1 and 3GlcNAcT in a sequential mode yielded 6-O-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.
Permanent Link: http://hdl.handle.net/11104/0260184