title: Chemoenzymatic synthesis of an N-acetylneuraminic acid analogue having a carbamoylmethyl group at C-4 as an inhibitor of sialidase from influenza virus.
abstract: 5,9-Diacetamido-2,6-anhydro-O-4-carbamoylmethyl-3,5,9-trideo xy-D-glycero- D-galacto-non-2-enonic acid (1) was synthesized via a key intemediate 2 through the Neu5Ac aldolase [E.C.4.1.3.3]-catalyzed aldol reaction of 2-acetamido-2,6-dideoxy-6-azido-D-glucose with sodium pyruvate operating under alkaline conditions (pH 10.5) in order to accelerate epimerization C-2 of N-acetyl-D-glucosamine (D-GlcNAc) derivatives. Compound 1 showed inhibitory activity against sialidase.
authors.affiliation: School of Pharmaceutical Sciences, University of Shizuoka, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Ikeda
authors.forename: F
authors.initials: F
authors.lastname: Kimura
authors.forename: K
authors.initials: K
authors.lastname: Sano
authors.forename: Y
authors.initials: Y
authors.lastname: Suzuki
authors.forename: K
authors.initials: K
authors.lastname: Achiwa
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D008956:Models, Chemical; D019158:N-Acetylneuraminic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000201:enzymology*; D007652:Oxo-Acid-Lyases / Q000378:metabolism
chemical_list: D004791:Enzyme Inhibitors; D009439:Neuraminidase; D007652:Oxo-Acid-Lyases; C018728:N-acetylneuraminate lyase; D019158:N-Acetylneuraminic Acid