The versatile enzyme Araf51 allowed efficient synthesis of rare pathogen-related β-D-galactofuranosyl-pyranoside disaccharides.
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.
Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 Allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France. vincent.ferrieres@ensc-rennes.fr.
Ilona
I
Chlubnová
Blanka
B
Králová
Hana
H
Dvořáková
Petr
P
Hošek
Vojtěch
V
Spiwok
Dominik
D
Filipp
Caroline
C
Nugier-Chauvin
Richard
R
Daniellou
Vincent
V
Ferrières
D055162:Biocatalysis; D004187:Disaccharides / Q000096:biosynthesis* / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000378:metabolism*; D056004:Molecular Dynamics Simulation; D013237:Stereoisomerism
D004187:Disaccharides; D006026:Glycoside Hydrolases