title: Transglycosylation of intact sialo complex-type oligosaccharides to the N-acetylglucosamine moieties of glycopeptides by Mucor hiemalis endo-beta-N-acetylglucosaminidase.
abstract: The endo-beta-N-acetylglucosaminidase (endo-beta-GlcNAc-ase) of Mucor hiemalis, endo-M, was found to transfer the sialo complex-type oligosaccharides from transferrin glycopeptide to the N-acetylglucosamine (GlcNAc) moieties of peptidyl-GlcNAc. Disialo complex-type oligosaccharide of transferrin glycopeptide was transferred to 9-fluorenylmethyloxycarbonyl (Fmoc)-asparaginyl-N-acetylglucosaminide (Fmoc-Asn-GlcNAc) by endo-M in a high yield. The structure of the reaction product was confirmed to be Fmoc-Asn-(GlcNAc)2-Man-(Man-GlcNac-Gal-NeuAc)2 by mass spectrometry. Endo-M also transferred disialo complex-type oligosaccharide to the GlcNAc residue of chemically synthesized H-Ile-Asn(GlcNAc)-Ala-Thr-Leu-OH. Asn-linked asialo complex-type oligosaccharide and Asn-linked high-mannose type oligosaccharide were also effective as oligosaccharide donors. Transfer of disialo complex-type oligosaccharide to the GlcNAc-peptide was the most effective among the three types of oligosaccharides, although the disialo complex-type oligosaccharide attached to the peptide was the poorest substrate for the hydrolytic activity of endo-M.
authors.affiliation: Hoguchi Institute, Tokyo, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Haneda
authors.forename: T
authors.initials: T
authors.lastname: Inazu
authors.forename: K
authors.initials: K
authors.lastname: Yamamoto
authors.forename: H
authors.initials: H
authors.lastname: Kumagai
authors.forename: Y
authors.initials: Y
authors.lastname: Nakahara
authors.forename: A
authors.initials: A
authors.lastname: Kobata
mesh_terms: D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000378:metabolism*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002851:Chromatography, High Pressure Liquid; D006020:Glycopeptides / Q000378:metabolism*; D006031:Glycosylation; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase / Q000378:metabolism*; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009089:Mucor / Q000201:enzymology; D009844:Oligosaccharides / Q000378:metabolism*; D012795:Sialoglycoproteins / Q000378:metabolism*
chemical_list: D006020:Glycopeptides; D009844:Oligosaccharides; D012795:Sialoglycoproteins; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase; D000117:Acetylglucosamine