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[21] Synthesis of poly( N -acetyl-β-lactosaminide-carrying acrylamide): Chemical-enzymatic hybrid process

Methods in Enzymology, ISSN: 0076-6879, Vol: 242, Issue: C, Page: 226-235
1994
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This chapter focuses on N -acetyllactosamine residues that are the major components of core oligosaccharides of glycoproteins and glycolipids and can serve as differentiation antigens, tumor-associated antigens, and components of receptor systems. Glycopolymers carrying pendant N -acetyllactosamine residues are expected to exhibit interesting functions in various biological recognition events. N -Acetyllactosamine was found in bovine colostrum as a free component and has been isolated from partial hydrolyzates of porcine gastric mucin and human milk. Several organic syntheses of N -acetyllactosamine have been developed by way of glycosylations between galactose and N -acetylglucosamine derivatives and chemical modifications of disaccharides because the yield of the disaccharide from natural products is insufficient. However, these tedious multistep procedures involving protections and deprotections are not well suited for large-scale productions. To overcome these difficulties, synthetic strategies using enzymes as catalysts have been introduced. Approaches using glycosyltransferases are promising, but the transferases and their cofactors as well as UDP-galactose are not readily available in large quantities.

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