150809-76-0Relevant articles and documents
Azido-phenylselenylation of protected glycals
Czernecki,Randriamandimby
, p. 7915 - 7916 (1993)
Anti-Markovnikov azido-phenylselenylation of diversely protected glycals affords protected phenyl 2-azido-2-deoxy-α-selenoglycopyranosides. From D-glucal, the α-manno and α-gluco isomers are obtained, whereas from D-galactal, a complete stereocontrol is observed, affording exclusively the α-galacto isomer in 70% yield.
Biotinylated Oligo-α-(1 → 4)-d-galactosamines and Their N-Acetylated Derivatives: α-Stereoselective Synthesis and Immunology Application
Kazakova, Ekaterina D.,Yashunsky, Dmitry V.,Krylov, Vadim B.,Bouchara, Jean-Philippe,Cornet, Murielle,Valsecchi, Isabel,Fontaine, Thierry,Latgé, Jean-Paul,Nifantiev, Nikolay E.
, p. 1175 - 1179 (2020)
Using 3-O-benzoyl-4,6-O-di-tert-butylsilylidene-2-azido-2-deoxy-selenogalactoside, biotinylated oligo-α-(1 → 4)-d-galactosamines comprising from two to six GalN units were prepared for the first time together with their N-acetylated derivatives. The combination of blocking groups used herein provided stereocontrol for the α-stereospecific glycosylation, to show also high efficiency of phenyl 2-azido-2-deoxy-selenogalactosides as glycosyl donors. The obtained glycoconjugates are related to fragments of exopolysaccharide galactosaminogalactan (GG) found in Aspergillus fumigatus, which is the most important airborne human fungal pathogen in industrialized countries. The synthesized glycoconjugates were arrayed on streptavidin-coated plates and used to investigate the GG epitopes recognized by mouse monoclonal antibodies against GG and by human antibodies in the sera of patients with aspergillosis. The obtained data showed that the oligo-α-(1 → 4)-d-galactosamines and their N-acetylated derivatives allowed the first precise analysis of the specificity of the antibody responses to this extremely complex fungal polysaccharide.
Safe and Scalable Continuous Flow Azidophenylselenylation of Galactal to Prepare Galactosamine Building Blocks
Guberman, Mónica,Pieber, Bartholom?us,Seeberger, Peter H.
, p. 2764 - 2770 (2019)
Differentially protected galactosamine building blocks are key components for the synthesis of human and bacterial oligosaccharides. The azidophenylselenylation of 3,4,6-tri-O-acetyl-d-galactal provides straightforward access to the corresponding 2-nitrog
Chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide
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Paragraph 0061; 0065, (2019/05/04)
The invention discloses a chemical synthesis method of Bacillus pyocyaneus 011 serotype O antigen oligosaccharide, and belongs to the field of chemistry. The method comprises the steps that a D-glucose block, an L-fucosamine block and a D-fucosimide block are utilized to construct O antigen trisaccharide, wherein the D-glucose block or the L-fucosamine block is connected with the D-fucosimide block through a 1,2-alpha-cis-glycosidic bond, the D-glucose block is connected with the L-fucososamine block through a 1,2-alpha-trans-glycosidic bond, and the 1,2-alpha-cis-glycosidic bond is constructed in a mixed solvent; the mixed solvent comprises two or more of dichloromethane, diethyl ether and thiophene. The method has the advantages that D-mannose is utilized as a raw material to obtain D-fucose simply, conveniently and efficiently; the uniform construction of the cis-glycosidic bond is achieved by relying on the appropriate mixed solvent; the stereoselectivity can reach 100%; and the method has a good application prospect in the development of novel drugs and vaccines for resisting Bacillus pyocyaneus and the like.
