32447-71-5Relevant academic research and scientific papers
From 1,4-Disaccharide to 1,3-Glycosyl Carbasugar: Synthesis of a Bespoke Inhibitor of Family GH99 Endo-α-mannosidase
Lu, Dan,Zhu, Sha,Sobala, Lukasz F.,Bernardo-Seisdedos, Ganeko,Millet, Oscar,Zhang, Yongmin,Jiménez-Barbero, Jesus,Davies, Gideon J.,Sollogoub, Matthieu
, p. 7488 - 7492 (2019/01/03)
Understanding the enzyme reaction mechanism can lead to the design of enzyme inhibitors. A Claisen rearrangement was used to allow conversion of an α-1,4-disaccharide into an α-1,3-linked glycosyl carbasugar to target the endo-α-mannosidase from the GH99 glycosidase family, which, unusually, is believed to act through a 1,2-anhydrosugar "epoxide" intermediate. Using NMR and X-ray crystallography, it is shown that glucosyl carbasugar α-aziridines can act as reasonably potent endo-α-mannosidase inhibitors, likely by virtue of their shape mimicry and the interactions of the aziridine nitrogen with the conserved catalytic acid/base of the enzyme active site.
Synthesis of 2-deoxy cyclic and linear oligosaccharides by oligomerization of monomers
Paul, Somak,Raghothama, Srinivasarao,Jayaraman, Narayanaswamy
experimental part, p. 177 - 186 (2009/04/11)
Cyclic and linear oligosaccharides constituted with 2-deoxy sugar units are synthesized by an oligomerization reaction involving activated thioglycoside monomers, consisting of a 2-deoxy sugar unit. The oligomerization promoter plays an important role in
Base-catalyzed degradation of permethylated 3-O-glycosylglycopyranosid-2-uloses
Aspinall,Capek,Carpenter,Szafranek
, p. 95 - 105 (2007/10/02)
In a modification of the Svensson degradation, otherwise permethylated glycopyranosid-2-uloses bearing 4-O-glycosyl substituents are formed by the Swern oxidation. Base-catalyzed elimination on treatment with triethylamine then gives 4-deoxy-3-O-methylglyc-3-enopyranosid-2-ulose-terminated oligosaccharides with liberation of glycosyl substituents as reducing sugars but without further degradation. Mild acid hydrolysis results in removal of the unsaturated sugar residues so that the overall depolymerization occurs with net loss of the initially oxidized sugar residue. In a modification of the Svensson degradation, otherwise permethylated glycopyranosid-2-uloses bearing 4-O-glycosyl substituents are formed by the Swern oxidation. Base-catalyzed elimination on treatment with triethylamine then gives 4-deoxy-3-O-methylglyc-3-enopyranosid -2-ulose-terminated oligosaccharides with liberation of glycosly substituents as reducing sugars but without further degradation. Mild acid hydrolysis results in removal of the unsaturated sugar residues so that the overall depolymerization occurs with net loss only of the initially oxidized sugar residue.
