Chemo-enzymatic synthesis of fluorinated 2-N-acetamidosugar nucleotides using UDP-GlcNAc pyrophosphorylase.
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).
Feng
Fei
F
Laboratory for Bio-Macromolecular Chemistry, Division of Biological Sciences, Graduate School of Science, Hokkaido University, Sapporo, Japan.
Okuyama
Kiyoshi
K
Niikura
Kenichi
K
Ohta
Takashi
T
Sadamoto
Reiko
R
Monde
Kenji
K
Noguchi
Toshitada
T
Nishimura
Shin-Ichiro
S
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
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