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On the observation of discrete fluorine NMR spectra for uridine 5'-?,?-fluoromethylenetriphosphate diastereomers at basic pH.

ABSTRACT: Jakeman et al. recently reported the inability to distinguish the diastereomers of uridine 5'-?,?-fluoromethylenetriphosphate (?,?-CHF-UTP, 1) by (19)F NMR under conditions we previously prescribed for the resolution of the corresponding ?,?-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.

SUBMITTER: Hwang CS

PROVIDER: S-EPMC4059216 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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On the observation of discrete fluorine NMR spectra for uridine 5'-β,γ-fluoromethylenetriphosphate diastereomers at basic pH.

Hwang Candy S CS Kashemirov Boris A BA McKenna Charles E CE

The Journal of organic chemistry 20140512 11

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 i ...[more]

PMID: 24819695

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