%0 Journal Article
%A Fauré, Régis
%A Saura-Valls, Marc
%A Brumer, Harry
%A Planas, Antoni
%A Cottaz, Sylvain
%A Driguez, Hugues
%D 2006
%T Synthesis of a Library of Xylogluco-Oligosaccharides for Active-Site
Mapping of Xyloglucan endo-Transglycosylase
%U https://acs.figshare.com/articles/journal_contribution/Synthesis_of_a_Library_of_Xylogluco_Oligosaccharides_for_Active_Site_Mapping_of_Xyloglucan_i_endo_i_Transglycosylase/3071878
%R 10.1021/jo0525682.s001
%2 https://acs.figshare.com/ndownloader/files/4777663
%K chemical synthesis
%K enzyme
%K Synthesi
%K oligosaccharide
%K degradation
%K compound
%K OH
%K yield
%K unsubstituted
%K terminal glucosyl units
%K fluoride
%K reaction product
%K Humicola insolens
%K donor synthon
%K enzymatically
%K residue
%K XET
%K plant cell wall biosynthesis
%K lactosyl motif
%K efficiency
%K acceptor
%K galactose
%K building blocks
%K synthesizing
%K Cel 7B E 197A glycosynthase
%K xyloglucan polymers
%K Constituting
%K site
%K target molecules
%K Mapping
%K modification
%K mapping
%K condensation
%K lactose
%K Xyloglucan
%X 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.
%I ACS Publications