441777-41-9

Upstream product

• 1187053-07-1 (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-1,2-O-allyloxyethylidene-4-O-benzyl-β-L-rhamnopyranose 
• 441777-40-8 allyl (2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-(1→3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside 

Downstream Products

• 441777-44-2 allyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside 
• 1061181-65-4 allyl (3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside 
• 1061181-62-1 allyl (3-O-acetyl-2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroacetamido)-β-D-glucopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside 
• 1091625-34-1 allyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-4-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranoside 
• 1095608-62-0 C₆₄H₇₅NO₁₈ 
• 1091625-54-5 allyl (2-deoxy-4,6-O-isopropylidene-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside 
• 1091625-13-6 allyl (2-deoxy-4,6-O-isopropylidene-2-(2,2,2-trichloroacetamido)-β-D-glucopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside 
• 1091625-12-5 allyl (2-deoxy-2-(2,2,2-trichloroacetamido)-β-D-glucopyranosyl)-(1->2)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)]-4-O-benzyl-α-L-rhamnopyranoside 
• 1106786-16-6 (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-4-O-benzyl-2-O-levulinoyl-α-L-rhamnopyranose 
• 1091625-35-2 (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-4-O-benzyl-2-O-levulinoyl-β-L-rhamnopyranose 

Relevant academic research and scientific papers

Glycoconjugates and use thereof as vaccine against Shigella flexneri serotype 3a and X

The present invention relates to compounds derived from sugars which reproduce the epitopes of Shigella flexneri serotypes 3a and X and to the use thereof for the preparation of vaccine compositions. More specifically, the subject matter of the present in

Design of α-transglucosidases of controlled specificity for programmed chemoenzymatic synthesis of antigenic oligosaccharides

Combined with chemical synthesis, the use of biocatalysts holds great potential to open the way to novel molecular diversity. We report in vitrochemoenzymatic pathways that, for the first time, take advantage of enz yme engineering to produce complex microbial cell-surface oligosaccharides and circumvent the chemical boundaries of glycochemistry. Glycoenzymes were designed to act on nonnatural conveniently protected substrates to produce intermediates compatible with a programmed chemical elongation. The study was focused on the synthesis of oligosaccharides mimicking the O-antigen motif of Shigella flexneri serotypes 1b and 3a, which couldbe used for the development of multivalent carbohydratebased vaccines. A semirational engineering approach was successfully applied to amylosuc rase, a transglucosidase that uses a low cost sucrose substrate as a glucosyl donor. The main difficulty was to retain the enzyme specificity toward sucrose, while creating a new catalytic function to render the enzyme able to regiospecifically glucosylate protected nonnatural acceptors.A structurally guided library of 133 mutants was generated from which s everal mutants with either completely new specificity toward methyl α-L-rhamnopyranoside or a tremendously enhanced one toward allyl 2-acetamido-2-deoxy-α-D-glucopyranoside acceptors were isolated. The best variants were used to synthesize glucosylated building blocks. They were then converted into acceptors and potential donors compatible with chemical elongation toward oligosaccharide fragments of the O-antigens ofthe two targeted serotypes. This is the first report of a successful en gineering of an α-transglycosidase acceptor binding site that led to new specificities. It demonstrates the potential of appropriate combinations of a planned chemoenzymatic pathway and enzyme engineering in glycochemistry.

Synthesis of branched tri- to pentasaccharides representative of fragments of Shigella flexneri serotypes 3a and/or X O-antigens

Fragments of the {2)-[α-d-Glcp-(1→3)]-α-l-Rhap-(1→2)-α-l-Rhap-(1→3)-[Ac→2]-α-l-Rhap-(1→3)-β-d-GlcpNAc-(1→}n ((E)ABAcCD)n polymer were synthesized. D(E)A, CD(E)A, AcCD(E)A were obtained according to a linear strategy, whereas BCD(E)A and BAcCD(E)A were derived from the condensation of appropriate BC and D(E)A building blocks. Oligosaccharides were synthesized as their propyl glycoside, relying on (i) the efficient trichloroacetimidate chemistry, (ii) a common EA allyl glycoside, and (iii) a 2-trichloroacetamido-d-glucopyranose precursor to residue D. Final Pd/C-mediated deprotection, run under a high pressure of hydrogen, ensured O-acetyl stability. All targets are parts of the O-antigen of Shigella flexneri 3a, a prevalent serotype. Non-O-acetylated oligosaccharides are shared by the S. flexneri serotype X O-antigen.

Synthesis and NMR study of a linear pentasaccharide fragment of the Shigella flexneri 5a O-specific polysaccharide

A convergent chemical synthesis of the methyl glycoside of the linear epitope α-D-Glcp-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap- (1→3)-β-D-GlcNAcp-(1→2)-α-L-Rhap (EBCDA) corresponding to the ramification of the O-antigen of Shigella flexneri serotype 5a is described