348145-58-4

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 348145-56-2 2-Bromoethyl 2-acetamido-2-deoxy-α-D-galactopyranoside 
• 72-87-7 N-acetyl-D-galactosamine 

Downstream Products

• 348145-70-0 C₅₉H₉₂N₁₂O₂₂S 
• 348145-60-8 2-Bromoethyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranoside 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of derivatives of a T-cell-stimulating peptide which carry tumor-associated carbohydrate antigens

The Tn (GalNAcα-Ser/Thr), T[Galβ(1→3)GalNAcβ-Ser/Thr], sialyl-Tn[Neu5Acα(2→6)GalNAcα-Ser/Thr] and 2,3-sialyl-T[Neu5Acα(2→3)Galβ(1→3)GalNAcα-Ser/Thr] antigens are examples of tumor-associated carbohydrate antigens expressed by epithelial cancers. We now describe the preparation of 2-bromoethyl glycosides corresponding to the Tn and T antigens in one and five chemical steps (51 and 15% total yield), respectively, starting from N-acetylgalactosamine. The 2-bromoethyl Tn and T glycosides were used to alkylate a homocysteine residue incorporated in a peptide that is able to bind to class I MHC molecules on antigen-presenting cells. The two neoglycopeptides were then converted into glycopeptides which carry the sialyl-Tn and 2,3-sialyl-T antigens by using recombinant sialyltransferases. Interestingly, the sialyltransferases were able to sialylate the Tn and T carbohydrate moieties even though they were linked to the peptide backbone via a spacer instead of being attached to serine or threonine. The four glycopeptides will be used in studies directed towards inducing a carbohydrate-specific T cell response against the Tn, T, sialyl-Tn, and 2,3-sialyl-T antigens.