Chemoenzymatic synthesis and application of a sialoglycopolymer with a chitosan backbone as a potent inhibitor of human influenza virus hemagglutination.
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.
Makimura
Yutaka
Y
Division of Life Science, Graduate School of Biostudies, Kyoto University, Sakyo-ku, Japan.
Watanabe
Shinya
S
Suzuki
Takashi
T
Suzuki
Yasuo
Y
Ishida
Hideharu
H
Kiso
Makoto
M
Katayama
Takane
T
Kumagai
Hidehiko
H
Yamamoto
Kenji
K
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
D009844:Oligosaccharides; D012795:Sialoglycoproteins; D048271:Chitosan; D017038:Mannosyl-Glycoprotein Endo-beta-N-Acetylglucosaminidase; D000117:Acetylglucosamine