Synthesis of a library of xylogluco-oligosaccharides for active-site mapping of xyloglucan endo-transglycosylase

Régis Fauré, Marc Saura-Valls, Harry Brumer, Antoni Planas, Sylvain Cottaz, Hugues Driguez

Research output: Indexed journal article Articlepeer-review

51 Citations (Scopus)

Abstract

Complex oligosaccharides containing α-D-xylosyl-(1→6)-β-D- glucosyl residues and unsubstituted β-(1→4)-linked D-glucosyl units were readily synthesized using enzymatic coupling catalyzed by the Cel7B E197A glycosynthase from Humicola insolens. Constituting this library required four key steps: (1) preparing unprotected building blocks by chemical synthesis or enzymatic degradation of xyloglucan polymers; (2) generating the donor synthon in the enzymatic coupling by temporarily introducing a lactosyl motif on the 4-OH of the terminal glucosyl units of the xylogluco-oligosaccharides; (3) synthesizing the corresponding α-fluorides, followed by their de-O-acetylation and the glycosynthase-catalyzed condensation of these donors onto various acceptors; and (4) enzymatically releasing lactose or galactose from the reaction product, affording the target molecules in good overall yields. These complex oligosaccharides proved useful for mapping the active site of a key enzyme in plant cell wall biosynthesis and modification: the xyloglucan endo-transglycosylase (XET). We also report some preliminary enzymatic results regarding the efficiency of these compounds.

Original languageEnglish
Pages (from-to)5151-5161
Number of pages11
JournalJournal of Organic Chemistry
Volume71
Issue number14
DOIs
Publication statusPublished - 7 Jul 2006

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