196397-63-4

Upstream product

• 16741-27-8 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide 
• 824-94-2 p-methoxybenzyl chloride 
• 167612-34-2 phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 
• 187233-24-5 phenyl 6-deoxy-1-thio-β-L-galactopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 73-34-7 6-deoxy-L-galactose 
• 196397-59-8 phenyl 3,4-O-isopropylidene-1-thio-β-L-fucopyranoside 

Downstream Products

• 196397-67-8 phenyl 6-deoxy-2-(4-methoxybenzyl)-1-thio-β-L-galactopyranoside 
• 1332865-57-2 C₃₉H₅₁NO₂₁ 
• 1332865-69-6 C₃₇H₄₈Cl₃NO₁₉ 
• 1332865-68-5 C₄₅H₅₆Cl₃NO₂₀ 
• 1332865-56-1 3,4-O-acetyl-2-O-p-methoxybenzyl-1-thiophenyl-β-L-fucopyranoside 
• 578738-14-4 C₅₇H₆₂O₂₀ 
• 578738-08-6 phenyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3-O-[3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl]-1-thio-β-D-glucopyranoside 
• 578738-09-7 allyl 2,6-di-O-benzoyl-4-O-(2,6-di-O-benzoyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-3-O-[3,4-O-isopropylidene-2-O-(4-methoxybenzyl)-α-L-fucopyranosyl]-β-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of Asparagine Derivatives Harboring a Lewis X Type DC-SIGN Ligand and Evaluation of their Impact on Immunomodulation in Multiple Sclerosis

The protein myelin oligodendrocyte glycoprotein (MOG) is a key component of myelin and an autoantigen in the disease multiple sclerosis (MS). Post-translational N-glycosylation of Asn31 of MOG seems to play a key role in modulating the immune response towards myelin. This is mediated by the interaction of Lewis-type glycan structures in the N-glycan of MOG with the DC-SIGN receptor on dendritic cells (DCs). Here, we report the synthesis of an unnatural Lewis X (LeX)-containing Fmoc-SPPS-compatible asparagine building block (SPPS=solid-phase peptide synthesis), as well as asparagine building blocks containing two LeX-derived oligosaccharides: LacNAc and Fucα1-3GlcNAc. These building blocks were used for the glycosylation of the immunodominant portion of MOG (MOG31-55) and analyzed with respect to their ability to bind to DC-SIGN in different biological setups, as well as their ability to inhibit the citrullination-induced aggregation of MOG31-55. Finally, a cytokine secretion assay was carried out on human monocyte-derived DCs, which showed the ability of the neoglycopeptide decorated with a single LeX to alter the balance of pro- and anti-inflammatory cytokines, inducing a tolerogenic response.

Synthesis of Lewis X trisaccharide analogues in which glucose and rhamnose replace N-acetylglucosamine and fucose, respectively

Two analogues of the Lex trisaccharide, α-L-Fucp-(1→3)-[β-D-Galp-(1→4)]-D-Glcp were synthesized as allyl glycosides. In these derivatives either only the N-acetylglucosamine is replaced by glucose or both the N-acetylglucosamine and the fucosyl residue are replaced by glucose and rhamnose, respectively. Our synthetic scheme used armed β-thiophenyl fuco- and rhamnoside glycosyl donors that were prepared anomerically pure from the corresponding α-glycosyl bromides. The protecting groups were chosen to allow access to the fully deprotected trisaccharides without reduction of the allyl glycosidic group. These analogues will be used as soluble antigens in binding experiments with anti-Lex antibodies and can also be conjugated to a carrier protein and used as immunogens. In the course of this synthetic work, we also describe the use of reversed-phase HPLC to purify key protected trisaccharide intermediates prior to their deprotection.