346435-08-3Relevant articles and documents
Synthesis of Glucuronoxylan Hexasaccharides by Preactivation-Based Glycosylations
B?hm, Maximilian,Madsen, Robert,Underlin, Emilie N.,d'Errico, Clotilde
supporting information, (2020/05/16)
The synthesis of two glucuronoxylans is described, which both consist of a pentaxylan backbone and a glucuronic acid linked to the 2 position in the fourth xylose residue from the reducing end. The two target molecules differ in the 4 position of the glucuronic acid where one is unsubstituted while the other contains a methyl ether. The pentaxylan backbone is assembled in four glycosylation reactions with phenyl thioglycoside donors. The couplings are performed by preactivation of the donor with in-situ-generated p-nitrobenzenesulfenyl triflate prior to addition of the acceptor. The glucuronic acids are then attached by Koenigs-Knorr glycosylations followed by deprotections. The syntheses employ a total of 8 steps from monosaccharide building blocks and afford the two glucuronoxylans in 12 and 15 % overall yield. The hexasaccharide products are valuable substrates for investigating the activity and specificity of glucuronoxylan-degrading enzymes.