title: A novel fluorescent derivative of glucose applicable to the assessment of glucose uptake activity of Escherichia coli.
abstract: A novel fluorescent derivative of glucose was synthesized by reacting D-glucosamine and NBD-Cl. The TLC analysis of the reaction mixture showed the generation of a single spot with intense fluorescence (lambda Ex = 475 nm, lambda Em = 550 nm). The obtained novel fluorescent product, which was identified as 2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose (2-NBDG) by 1H-NMR and FAB-MS spectrometries, was applied to the assessment of the glucose uptake activity of Escherichia coli B. 2-NBDG accumulated in living cells and not in dead cells. The uptake of 2-NBDG was competitively inhibited by D-glucose and not by L-glucose, which suggested the involvement of the glucose transporting system in the uptake of 2-NBDG. 2-NBDG taken into the cytoplasma of E. coli cells was supposedly converted into another derivative in the glucose metabolic pathway.
authors.affiliation: Department of Biotechnology, Tokyo University of Agriculture and Technology, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Yoshioka
authors.forename: H
authors.initials: H
authors.lastname: Takahashi
authors.forename: T
authors.initials: T
authors.lastname: Homma
authors.forename: M
authors.initials: M
authors.lastname: Saito
authors.forename: K B
authors.initials: KB
authors.lastname: Oh
authors.forename: Y
authors.initials: Y
authors.lastname: Nemoto
authors.forename: H
authors.initials: H
authors.lastname: Matsuoka
mesh_terms: D009327:4-Chloro-7-nitrobenzofurazan / Q000031:analogs & derivatives* / Q000378:metabolism; D003847:Deoxyglucose / Q000031:analogs & derivatives* / Q000378:metabolism; D004926:Escherichia coli / Q000378:metabolism*; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000378:metabolism*; D005947:Glucose / Q000378:metabolism*
chemical_list: D005456:Fluorescent Dyes; D003847:Deoxyglucose; D009327:4-Chloro-7-nitrobenzofurazan; D005947:Glucose; C098340:2-(N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl)amino)-2-deoxyglucose