Issue 19, 2014

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

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

Article information

Article type
Paper
Submitted
17 Dec 2013
Accepted
21 Feb 2014
First published
21 Feb 2014
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2014,12, 3080-3089

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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