title: On the observation of discrete fluorine NMR spectra for uridine 5'-β,γ-fluoromethylenetriphosphate diastereomers at basic pH.
abstract: Jakeman et al. recently reported the inability to distinguish the diastereomers of uridine 5'-β,γ-fluoromethylenetriphosphate (β,γ-CHF-UTP, 1) by (19)F NMR under conditions we previously prescribed for the resolution of the corresponding β,γ-CHF-dGTP spectra, stating further that 1 decomposed under these basic conditions. Here we show that the (19)F NMR spectra of 1 (~1:1 diastereomer mixture prepared by coupling of UMP-morpholidate with fluoromethylenebis(phosphonic acid)) in D2O at pH 10 are indeed readily distinguishable. 1 in this solution was stable for 24 h at rt.
authors.affiliation: Department of Chemistry, University of Southern California , Los Angeles, California 90089, United States.
authors.forename: Candy S
authors.initials: CS
authors.lastname: Hwang
authors.forename: Boris A
authors.initials: BA
authors.lastname: Kashemirov
authors.forename: Charles E
authors.initials: CE
authors.lastname: McKenna
mesh_terms: D003848:Deoxyguanine Nucleotides / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D013237:Stereoisomerism; D014500:Uracil Nucleotides / Q000737:chemistry*; D014529:Uridine / Q000737:chemistry*
chemical_list: D003848:Deoxyguanine Nucleotides; D014500:Uracil Nucleotides; C000594714:uridine 5'-beta,gamma-fluoromethylenetriphosphate; D005461:Fluorine; C029603:deoxyguanosine triphosphate; D014529:Uridine