116490-75-6

Upstream product

• 329006-48-6 5-O-allyl-2,3-di-O-benzyl-β-D-ribofuranose 
• 116490-68-7 Methyl 5-O-allyl-D-ribofuranoside 
• 100-39-0 benzyl bromide 
• 116490-72-3 (2R,3R,4R,5R)-2-(allyloxymethyl)-3,4-bis(benzyloxy)-5-methoxytetrahydrofuran 
• 116490-68-7 methyl 5-O-allyl-D-ribofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 114488-50-5 β-5-O-allyl-1-O-methyl-2,3-O,O-isopropylidene-D-ribofuranoside 

Downstream Products

• 111549-97-4 2,3,4-Tris-O-(phenylmethyl)-5-O-(prop-2-enyl)-D-ribitol 
• 116490-76-7 5-O-allyl-1,2,3-tri-O-benzyl-D-ribitol 
• 329006-49-7 C₄₁H₄₂O₅ 
• 134340-31-1 1-O-acetyl-2,3-di-O-benzyl-4-O-<2,4-di-O-acetyl-3-O-<2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-glucopyranosyl>-α-L-rhamnopyranosyl>-D-ribitol 
• 134340-29-7 5-O-allyl-2,3-di-O-benzyl-4-O-<2,4-di-O-acetyl-3-O-<2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-glucopyranosyl>-α-L-rhamnopyranosyl>-D-ribitol 
• 134340-33-3 1-O-acetyl-2,3-di-O-benzyl-4-O-<2,4-di-O-acetyl-3-O-<2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-glucopyranosyl>-α-L-rhamnopyranosyl>-D-ribitol 5-(triethylammonium phosphonate) 
• 134365-05-2 5-O-allyl-1-O-allyloxycarbonyl-2,3-di-O-benzyl-4-O-<2,4-di-O-acetyl-3-O-<2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-α-D-glucopyranosyl>-α-L-rhamnopyranosyl>-D-ribitol 
• 134340-30-0 C₆₀H₇₈O₂₉ 
• 212127-43-0 C₇₁H₇₈NO₁₄P 
• 104972-91-0 1,2,3,4-Tetra-O-benzyl-D-ribitol 
• 154618-60-7 5-O-allyl-1,2,3,4-tetra-O-benzyl-D-ribitol 
• 134340-26-4 5-O-allyl-1-O-allyloxycarbonyl-2,3-di-O-benzyl-D-ribitol 

Relevant academic research and scientific papers

(Automated) Synthesis of Well-defined Staphylococcus Aureus Wall Teichoic Acid Fragments

Wall teichoic acids (WTAs) are important components of the cell wall of the opportunistic Gram-positive bacterium Staphylococcus aureus. WTAs are composed of repeating ribitol phosphate (RboP) residues that are decorated with d-alanine and N-acetyl-d-glucosamine (GlcNAc) modifications, in a seemingly random manner. These WTA-modifications play an important role in shaping the interactions of WTA with the host immune system. Due to the structural heterogeneity of WTAs, it is impossible to isolate pure and well-defined WTA molecules from bacterial sources. Therefore, here synthetic chemistry to assemble a broad library of WTA-fragments, incorporating all possible glycosylation modifications (α-GlcNAc at the RboP C4; β-GlcNAc at the RboP C4; β-GlcNAc at the RboP C3) described for S. aureus WTAs, is reported. DNA-type chemistry, employing ribitol phosphoramidite building blocks, protected with a dimethoxy trityl group, was used to efficiently generate a library of WTA-hexamers. Automated solid phase syntheses were used to assemble a WTA-dodecamer and glycosylated WTA-hexamer. The synthetic fragments have been fully characterized and diagnostic signals were identified to discriminate the different glycosylation patterns. The different glycosylated WTA-fragments were used to probe binding of monoclonal antibodies using WTA-functionalized magnetic beads, revealing the binding specificity of these WTA-specific antibodies and the importance of the specific location of the GlcNAc modifications on the WTA-chains.

Oligosaccharides derived from ribose-ribitol-phosphate, and vaccines containing them

The present invention relates to the field of the Medicine, in particular with the chemical synthesis of oligosaccharide mixtures derived of ribose-ribitol-phosphate, which are used as active principle in vaccines for the prevention of infections caused byHaemophilus influenzaetype b (Hib), as well as with the vaccines containing said oligosaccharide mixtures. The oligasaccharide mixtures obtained by chemical synthesis of the present invention, comprise repeating units of formulae (phosphate-ribosa-ribitol)n or (ribose-ribitol-phosphate)n of at least 5 compounds of structure A or B, which represent the repeating unit of the capsular polysaccharide ofHaemophilus influenzaetype b and differ only by n, being n a value contained between 4 and 25 (n≧4 y≦25), and wherein R1or R2is a spacer for conjugation to a carrier, with the condition of R1=spacer if R2=H, or R2=spacer if R1=H. The invention also is related with the immunogens containing such oligosaccharide mixtures, with the vaccines containing said immunogens and with the methods to prepare these oligosaccharides as mixtures. Furthermore, the invention includes the use of the vaccines, alone or combined with other vaccines, for the prevention of the infections caused byHaemophilus influenzaetype b.

The synthesis of two repeating units of Haemophilus influenzae type a capsular antigen.

The repeating units 2-O-beta-D-glucopyranosyl-L-ribitol 4'- and 1-phosphate of Haemophilus influenzae type a capsular antigen have been synthesised by condensation of an alpha-D-glucopyranosyl bromide derivative with 5-O-allyl-1,2,3-tri-O-benzyl-D-ribitol followed by selective deprotection of HO-4' or HO-1, phosphorylation, and removal of the blocking groups.