188641-24-9

Upstream product

• 106-95-6 allyl bromide 
• 501-53-1 benzyl chloroformate 
• 17041-36-0 3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-L-serin 

Downstream Products

• 188641-26-1 N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester 
• 460729-19-5 N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-3-nonulopyranosylonic acid)-(2->6)]-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine 
• 220414-49-3 N-(benzyloxycarbonyl)-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester 

Relevant academic research and scientific papers

Chemoenzymatic synthesis of NeuAcα-(2→3)-Galβ-(1→3)-[NeuAcα-(2→6)]- GalNAcα1-O-(Z)-Serine (N-protected MUC II oligosaccharide-serine)

An efficient synthesis of NeuAcα-(2→3)-Galβ-(1→3)-[NeuAcα-(2→6)]- GalNAcα1-O-(Z)-Serine (N-protected MUC II oligosaccharide-serine, 14) by a chemoenzymatic strategy is described. The enzymatic reaction of GalNAcα1-O-(Z)-Ser-OAll 7 with pNP-β-Gal in the presence of recombinant β1,3-galactosidase from Bacillus circulans gave Galβ-(1→3)-GalNAcα1-O-(Z)-Ser-O All3 in 68%. The introduction of two sialic acids into 3 was accomplished by a stepwise method. The branched Galβ-(1→3)-[NeuAcα-(2→6)]-GalNAcα1-O-(Z)-Ser-OAll 11 was constructed by a chemical method. Sialylation at the C-3 position of the terminal Gal residue on Galβ-(1→3)-[NeuAcα-(2→6)]-GalNAcα1-O-(Z)-Serine 2 using α2,3-(O)-sialyltransferase from rat liver gave a target compound 14 in a practical yield.

An efficient synthesis of a Galβ1-3GalNAc-serine derivative using β-galactosidase

An efficient route for the synthesis of Galβ1-3GalNAcα1-O-serine derivative was developed using a novel β1-3 galactosidase obtained from Bacillus circulans. By a transglycosylation reaction with pNP-β-Gal 2 as a donor and GalNAcα1-O-Z-Ser-OAll 4 as an acceptor, Galβ1-3GalNAcα-1-O-Z-Ser-OAll 5 was synthesized in 68% yield.