title: Chemo-enzymatic synthesis of fluorinated 2-N-acetamidosugar nucleotides using UDP-GlcNAc pyrophosphorylase.
abstract: Two non-natural fluorinated 2-N-acetamidosugar nucleotides, uridine 5'-diphosphate (UDP) 2-acetamido-2,4-dideoxy-4-fluoro-alpha-D-glucopyranose (UDP-4-FGlcNAc) 1 and its galacto isomer (UDP-4-FGalNAc) 2, were enzymatically constructed by treating chemically synthesized fluorinated 2-N-acetamidosugar 1-phosphates as the donor with UDP 2-acetamido-2-deoxy-alpha-D-glucopyranose pyrophosphorylase in the presence of uridine 5'-triphosphate (UTP).
authors.affiliation: Laboratory for Bio-Macromolecular Chemistry, Division of Biological Sciences, Graduate School of Science, Hokkaido University, Sapporo, Japan.
authors.forename: Fei
authors.initials: F
authors.lastname: Feng
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Okuyama
authors.forename: Kenichi
authors.initials: K
authors.lastname: Niikura
authors.forename: Takashi
authors.initials: T
authors.lastname: Ohta
authors.forename: Reiko
authors.initials: R
authors.lastname: Sadamoto
authors.forename: Kenji
authors.initials: K
authors.lastname: Monde
authors.forename: Toshitada
authors.initials: T
authors.lastname: Noguchi
authors.forename: Shin-Ichiro
authors.initials: S
authors.lastname: Nishimura
mesh_terms: D000116:Acetylgalactosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D000117:Acetylglucosamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D002236:Carbohydrate Conformation; D004926:Escherichia coli / Q000201:enzymology; D009713:Nucleotidyltransferases / Q000378:metabolism*; D014530:Uridine Diphosphate / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000378:metabolism; D014544:Uridine Triphosphate / Q000737:chemistry
chemical_list: C488435:uridine 5'-diphosphate 2-acetamido-2,4-dideoxy-4-fluorogalactopyranose; C488434:uridine 5'-diphosphate 2-acetamido-2,4-dideoxy-4-fluoroglucopyranose; D014530:Uridine Diphosphate; D009713:Nucleotidyltransferases; C023226:UDPacetylglucosamine pyrophosphorylase; D000116:Acetylgalactosamine; D014544:Uridine Triphosphate; D000117:Acetylglucosamine