On the Observation of Discrete Fluorine NMR Spectra for Uridine 5′-β,γ-Fluoromethylenetriphosphate Diastereomers at Basic pH | Zendy

Candy S. Hwang | Zendy; B. A. Kashemirov | Zendy; Charles E. McKenna | Zendy

Open Access

On the Observation of Discrete Fluorine NMR Spectra for Uridine 5′-β,γ-Fluoromethylenetriphosphate Diastereomers at Basic pH

Author(s) -

Candy S. Hwang,

B. A. Kashemirov,

Charles E. McKenna

Publication year - 2014

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/jo500452b

Subject(s) - diastereomer , chemistry , nmr spectra database , uridine , fluorine 19 nmr , spectral line , nuclear magnetic resonance spectroscopy , chemical shift , fluorine , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , organic chemistry , rna , biochemistry , physics , astronomy , gene

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.

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