A chemoenzymatic approach for the synthesis of unnatural dissacharides containing D-galacto- or D-fucofuranosides - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Accéder directement au contenu
Article Dans Une Revue Global Change Biology Année : 2005

A chemoenzymatic approach for the synthesis of unnatural dissacharides containing D-galacto- or D-fucofuranosides

Résumé

Unusual diglycosides composed of D-hexofuranosyl entities were prepared by a chemoenzymatic route using the alpha-L-arabinofuranosidase, AbfD3. The required, unprotected monosaccharidic donors were first prepared according to multi-step syntheses. Since one goal of this study was the investigation of donor -1 subsite in the active site of the enzyme, we focused on D-fucofuranosyl and 6-deoxy-6-fluoro-D-galactofuranosyl derivatives which present stereochemical similarities with L-arabinose series, but also structural variations on the side arm. These substrates were then used in AbfD3-catalysed hydrolyses to determine the parameters Km and kcat and in AbfD3-catalysed transglycosylation to evaluate their ability to serve as donor/acceptor. Four disaccharides were thus isolated and characterised, two resulting from beta-(1,2) connection along with two beta-(1,3)-regioisomers.

Dates et versions

hal-02682640 , version 1 (01-06-2020)

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Citer

Ronan Euzen, Gérald Lopez, Caroline Nugier-Chauvin, Vincent Ferrières, Daniel Plusquellec, et al.. A chemoenzymatic approach for the synthesis of unnatural dissacharides containing D-galacto- or D-fucofuranosides. Global Change Biology, 2005, 2005 (22), pp.4860-4869. ⟨10.1002/ejoc.200500525⟩. ⟨hal-02682640⟩
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