1616627-99-6

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 1616627-97-4 dimethylthexylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranoside 
• 219693-02-4 1,3,4,6-tetra-O-acetyl-2-deoxy-2-trichloroacetamido-α/β-D-glucopyranose 

Downstream Products

• 1616628-00-2 dimethylthexylsilyl 4,6-O-benzylidene-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 
• 1616628-01-3 dimethylthexylsilyl 6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranoside 
• 1616628-05-7 benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-3-O-levulinoyl-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate 
• 1616628-06-8 benzyl [4-methoxyphenyl 2-O-benzoyl-3-O-benzyl-4-O-(4-O-acetyl-6-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-β-D-glucopyranoside]uronate 
• 1616628-02-4 C₃₀H₄₄Cl₃NO₉Si 

Relevant academic research and scientific papers

4,6- O-Pyruvyl Ketal Modified N-Acetylmannosamine of the Secondary Cell Wall Polysaccharide of Bacillus anthracis Is the Anchoring Residue for Its Surface Layer Proteins

The secondary cell wall polysaccharide (SCWP) of Bacillus anthracis plays a key role in the organization of the cell envelope of vegetative cells and is intimately involved in host-guest interactions. Genetic studies have indicated that it anchors S-layer and S-layer-associated proteins, which are involved in multiple vital biological functions, to the cell surface of B. anthracis. Phenotypic observations indicate that specific functional groups of the terminal unit of SCWP, including 4,6-O-pyruvyl ketal and acetyl esters, are important for binding of these proteins. These observations are based on genetic manipulations and have not been corroborated by direct binding studies. To address this issue, a synthetic strategy was developed that could provide a range of pyruvylated oligosaccharides derived from B. anthracis SCWP bearing base-labile acetyl esters and free amino groups. The resulting oligosaccharides were used in binding studies with a panel of S-layer and S-layer-associated proteins, which identified structural features of SCWP important for binding. A single pyruvylated ManNAc monosaccharide exhibited strong binding to all proteins, making it a promising structure for S-layer protein manipulation. The acetyl esters and free amine of SCWP did not significantly impact binding, and this observation is contrary to a proposed model in which SCWP acetylation is a prerequisite for association of some but not all S-layer and S-layer-associated proteins.

Synthesis of hyaluronic acid oligosaccharides and exploration of a fluorous-assisted approach

The synthesis of hyaluronic acid oligomers (tri- and tetrasaccharide) is described. We have followed a pre-glycosylation oxidation strategy. Glucuronic acid units were directly employed in coupling reactions with suitably protected glucosamine derivatives. In order to simplify the purification of synthetic intermediates, a fluorous-assisted strategy has been also explored. Using this approach, a hyaluronic acid trisaccharide was prepared.