title: Synthesis of neoproteoglycans using the transglycosylation reaction as a reverse reaction of endo-glycosidases.
abstract: A method for the synthesis of carbohydrate chains (glycosaminoglycans) and their coupling to peptides was investigated using proteoglycans. Glycosidases generally catalyze a hydrolytic reaction, but can also mediate the reverse reaction, which in this case is a transglycosylation. In the transglycosylation reaction of bovine testicular hyaluronidase, which is an endoglycosidase, glycosaminoglycans (hyaluronan and chondroitin sulfates) release disaccharide (uronic acid-N-acetylhexosamine) moieties from non-reducing terminal sites, and then the liberated disaccharides are transferred immediately to the non-reducing termini of other glycosaminoglycan chains. Using such continuous reactions, it is possible to synthesize glycosaminoglycan chains according to a specific design. It then becomes possible to transfer glycosaminoglycan chains synthesized on a peptide to other peptides using the transglycosylation reaction of endo-β-xylosidase acting on the linkage region between a peptide and glycosaminoglycan chains of proteoglycans. We believe this approach will open a new field for the synthesis of homogeneous proteoglycans or their corresponding analogues.
authors: Department of Glycobiochemistry, Hirosaki University Graduate School of Medicine, Hirosaki, Japan. endom@cc.hirosaki-u.ac.jp
authors: Masahiko
authors: M
authors: Endo
authors: Ikuko
authors: I
authors: Kakizaki
mesh_terms: D002240:Carbohydrate Sequence; D006025:Glycosaminoglycans / Q000378:metabolism; D006026:Glycoside Hydrolases / Q000378:metabolism*; D006031:Glycosylation; D008969:Molecular Sequence Data; D010455:Peptides / Q000737:chemistry / Q000378:metabolism; D011509:Proteoglycans / Q000096:biosynthesis* / Q000737:chemistry
chemical_list: D006025:Glycosaminoglycans; D010455:Peptides; D011509:Proteoglycans; D006026:Glycoside Hydrolases