Literature DB >> 32390019

Chemoenzymatic synthesis of 3-deoxy-3-fluoro-l-fucose and its enzymatic incorporation into glycoconjugates.

Pablo Valverde1, Jean-Baptiste Vendeville2, Kristian Hollingsworth3, Ashley P Mattey4, Tessa Keenan5, Harriet Chidwick5, Helene Ledru6, Kler Huonnic2, Kun Huang4, Mark E Light2, Nicholas Turner4, Jesús Jiménez-Barbero7, M Carmen Galan6, Martin A Fascione5, Sabine Flitsch4, W Bruce Turnbull3, Bruno Linclau2.   

Abstract

The first synthesis of 3-deoxy-3-fluoro-l-fucose is presented, which employs a d- to l-sugar translation strategy, and involves an enzymatic oxidation of 3-deoxy-3-fluoro-l-fucitol. Enzymatic activation (FKP) and glycosylation using an α-1,2 and an α-1,3 fucosyltransferase to obtain two fluorinated trisaccharides demonstrates its potential as a novel versatile chemical probe in glycobiology.

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Year:  2020        PMID: 32390019     DOI: 10.1039/d0cc02209h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  1 in total

1.  Synthesis of Four Orthogonally Protected Rare l-Hexose Thioglycosides from d-Mannose by C-5 and C-4 Epimerization.

Authors:  Fruzsina Demeter; Ilona Bereczki; Anikó Borbás; Mihály Herczeg
Journal:  Molecules       Date:  2022-05-25       Impact factor: 4.927

  1 in total

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