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Issue 19, 2014
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The versatile enzyme Araf51 allowed efficient synthesis of rare pathogen-related β-D-galactofuranosyl-pyranoside disaccharides

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Abstract

The preparation of galactofuranosyl-containing disaccharidic parts of natural glycoconjugates was performed according to a chemo-enzymatic synthesis. Our goals were firstly to develop an alternative approach to standard chemical strategies by limiting the number of reaction and purification steps, and secondly to evaluate the scope of the Araf51 biocatalyst to transfer a galactofuranosyl moiety to a set of pyranosidic acceptors differing from each other by the series, the anomeric configuration as well as the conformation. The study of binding mode of the resulting disaccharides was also performed by molecular modeling and showed significant differences between (1→2)- and (1→6)-linked disaccharides.

Graphical abstract: The versatile enzyme Araf51 allowed efficient synthesis of rare pathogen-related β-d-galactofuranosyl-pyranoside disaccharides

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Publication details

The article was received on 17 Dec 2013, accepted on 21 Feb 2014 and first published on 21 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42519C
Citation: Org. Biomol. Chem., 2014,12, 3080-3089
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    The versatile enzyme Araf51 allowed efficient synthesis of rare pathogen-related β-D-galactofuranosyl-pyranoside disaccharides

    I. Chlubnová, B. Králová, H. Dvořáková, P. Hošek, V. Spiwok, D. Filipp, C. Nugier-Chauvin, R. Daniellou and V. Ferrières, Org. Biomol. Chem., 2014, 12, 3080
    DOI: 10.1039/C3OB42519C

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