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, <b>1</b>) by ¹⁹F NMR under conditions we previously prescribed for the resolution of the corresponding β,γ-CHF-dGTP spectra, stating further that <b>1</b> decomposed under these basic conditions. Here we show that the ¹⁹F NMR spectra of <b>1</b> (∼1:1 diastereomer mixture prepared by coupling of UMP-morpholidate with fluoro­methylene­bis­(phos­phonic acid)) in D₂O at pH 10 are indeed readily distinguishable. <b>1</b> in this solution was stable for 24 h at rt