83982-55-2

Upstream product

• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 
• 84500-41-4 N-benzyloxycarbonyl-L-threonine benzyl ester 
• 83025-11-0 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate 

Downstream Products

• 83982-56-3 O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 83956-44-9 3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 83956-46-1 3-O-(2-Acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 83956-45-0 3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 60280-58-2 O-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant

The efficient chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant is demonstrated under transglycosylation conditions employing β-galactosidase from bovine testes.

Synthesis of the glycopeptide O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-desoxy-alpha-D-galactopyranosyl)-(1 to 3)-L-serine and -L-threonine

In the presence of silver carbonate-silver perchlorate and dichloromethane-toluene as solvent, 3,4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranosyl chloride, and derivatives of L-serine and -L-serine and -L-threonine, gave, with high stereoselectivity, the benzyl esters of N-(benzyloxycarbonyl)-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl)-L-serine (7) and -L-threonine (22), which were hydrogenolyzed and deblocked to give 3-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-serine and -L-threonine, respectively, corresponding to the hapten of the Tn-antigen. Reduction of the azido group of 7, followed by selective O-deacetylation and benzylidenation, gave a derivative that was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide to yield a disaccharide. A similar sequence of reactions, starting from 22, gave the L-threonine analog. Removal of the protecting groups from both compounds afforded O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-serine and -L-serine and -L-threonine, respectively, the hapten of the T-antigen.