70932-43-3

Upstream product

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-L-galactopyranose 
• 100-39-0 benzyl bromide 
• 110319-61-4 1,2:3,4-di-O-isopropylidene-β-D-galactopyranose 
• 10257-28-0 D-Galactose 

Downstream Products

• 6207-46-1 allyl 6-O-benzyl-α-D-galactopyranoside 
• 290330-34-6 2,3,4-tri-O-acetyl-6-O-benzyl-α-D-galactopyranosyl bromide 
• 142800-31-5 <(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>-<(2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose 
• 142800-33-7 <(6-deoxy-2,3,4-tri-O-benzyl-α-L-galactopyranosyl)-(1->3)>-<(6-O-benzyl-β-D-galactopyranosyl)-(1->4)>-1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranose 
• 196942-01-5 1,2,3,4-tetra-O-acetyl- 6-O-benzyl-α/β-D-galactopyranoside 
• 20675-63-2 6-O-benzyl-D-galactose 
• 142800-27-9 2,3,4-tri-O-benzoyl-6-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 
• 20675-63-2 (3S,4R,5S,6S)-6-Benzyloxymethyl-tetrahydro-pyran-2,3,4,5-tetraol 

Relevant academic research and scientific papers

Synthesis of phosphoric acid diesters of 7β-hydroxycholesterol and of carbohydrates

In order to enhance the antitumor efficacy of 7β-hydroxycholesterol by targeting its action to defined organs, the phosphoric acid esters of 3(7β-hydroxycholesteryl) and of 6(galactopyranosyl) 1 or 6(mannopyranosyl) 2 were synthesized by the phosphoramidi

Synthetic MUC1 antitumor vaccine with incorporated 2,3-sialyl-T carbohydrate antigen inducing strong immune responses with isotype specificity

The endothelial glycoprotein MUC1 is known to underlie alterations in cancer by means of aberrant glycosylation accompanied by changes in morphology. The heavily shortened glycans induce a collapse of the peptide backbone and enable accessibility of the latter to immune cells, rendering it a tumor-associated antigen. Synthetic vaccines based on MUC1 tandem repeat motifs, comprising tumor-associated 2,3-sialyl-T antigen, conjugated to the immunostimulating tetanus toxoid, are reported herein. Immunization with these vaccines in a simple water/oil emulsion produced a strong immune response in mice to which stimulation with complete Freund’s adjuvant (CFA) was not superior. In both cases, high levels of IgG1 and IgG2a/b were induced in C57BL/6 mice. Additional glycosylation in the immunodominant PDTRP domain led to improved binding of the induced antisera to MCF-7 breast tumor cells, compared with that of the monoglycosylated peptide vaccine.

METHODS AND COMPOSITIONS FOR MAKING ANTIBODIES AND ANTIBODY DERIVATIVES WITH REDUCED CORE FUCOSYLATION

The invention provides methods and compositions for preparing antibodies and antibody derivatives with reduced core fucosylation.

C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis

O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis olefination of glyconolactones, stereoselective hydroboration and a mild B-alkyl-Suzuki coupling reaction. The coupling products were transformed to C-glycosyl amino acid building-blocks suitable for solid-phase synthesis and successfully incorporated into a partial sequence of the tumor-associated MUC1-glycopeptide. The resulting C-glycopeptides are candidates for the development of long-term stable mimics of O-glycopeptide vaccines. Copyright