title: Chemoenzymatic synthesis and application of a sialoglycopolymer with a chitosan backbone as a potent inhibitor of human influenza virus hemagglutination.
abstract: Sialoglycopeptide (SGP) is referred as the glycopeptide in hen's egg yolk, which has an N-linked, complex-type, disialyl biantennary oligosaccharide with an alpha-(2-->6)-sialyl N-acetyllactosamine residue. The residue is known as a binding ligand of type-A human influenza virus hemagglutinin. We describe herein a simple synthesis of a sialoglycopolymer with a chitosan backbone as a potent inhibitor of human influenza virus hemagglutination that makes use of the natural source ingredient, SGP, and the transglycosylation activity of endo-beta-N-acetylglucosaminidase from Mucor hiemalis (Endo-M). Its inhibitiory activity for influenza virus hemagglutination is 40 times higher than that of SGP, and its competitive inhibition is determined to be over 300 times higher than that of fetuin. These results indicate that a sialoglycopolymer having a multivalent sialo-oligosaccharide could potentially be used for the prevention of influenza virus infection.
authors.affiliation: Division of Life Science, Graduate School of Biostudies, Kyoto University, Sakyo-ku, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Makimura
authors.forename: Shinya
authors.initials: S
authors.lastname: Watanabe
authors.forename: Takashi
authors.initials: T
authors.lastname: Suzuki
authors.forename: Yasuo
authors.initials: Y
authors.lastname: Suzuki
authors.forename: Hideharu
authors.initials: H
authors.lastname: Ishida
authors.forename: Makoto
authors.initials: M
authors.lastname: Kiso
authors.forename: Takane
authors.initials: T
authors.lastname: Katayama
authors.forename: Hidehiko
authors.initials: H
authors.lastname: Kumagai
authors.forename: Kenji
authors.initials: K
authors.lastname: Yamamoto
mesh_terms: D000117:Acetylglucosamine / Q000737:chemistry; D000818:Animals; D002240:Carbohydrate Sequence; D048271:Chitosan / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D004912:Erythrocytes / Q000187:drug effects / Q000276:immunology; D006168:Guinea Pigs; D006384:Hemagglutination / Q000187:drug effects*; D006385:Hemagglutination Inhibition Tests; D006801:Humans; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase / Q000378:metabolism; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009975:Orthomyxoviridae / Q000187:drug effects / Q000276:immunology*; D012795:Sialoglycoproteins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D009844:Oligosaccharides; D012795:Sialoglycoproteins; D048271:Chitosan; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase; D000117:Acetylglucosamine