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Towards Keratan Sulfate - Chemoenzymatic Cascade Synthesis of Sulfated N-Acetyllactosamine (LacNAc) Glycan Oligomers
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SYSNO ASEP 0460034 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Towards Keratan Sulfate - Chemoenzymatic Cascade Synthesis of Sulfated N-Acetyllactosamine (LacNAc) Glycan Oligomers Author(s) Lange, B. (DE)
Šimonová, Anna (MBU-M)
Fischoeder, T. (DE)
Pelantová, Helena (MBU-M) ORCID, RID
Křen, Vladimír (MBU-M) RID, ORCID
Elling, L. (DE)Source Title Advanced Synthesis & Catalysis. - : Wiley - ISSN 1615-4150
Roč. 358, č. 4 (2016), s. 584-596Number of pages 13 s. Language eng - English Country DE - Germany Keywords biocatalysis ; carbohydrates ; glycoconjugates Subject RIV CE - Biochemistry R&D Projects LD13042 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) GC15-02578J GA ČR - Czech Science Foundation (CSF) Institutional support MBU-M - RVO:61388971 UT WOS 000371665800013 EID SCOPUS 84958753505 DOI 10.1002/adsc.201500916 Annotation 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. Workplace Institute of Microbiology Contact Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231 Year of Publishing 2017
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