4627-40-1Relevant articles and documents
Synthesis of Trifluoromethylated Purine Ribonucleotides and Their Evaluation as 19F NMR Probes
Baranowski, Marek R.,Chmielinski, Sebastian,Chrominski, Mikolaj,Jemielity, Jacek,Kowalska, Joanna
, p. 3440 - 3453 (2020)
Protected guanosine and adenosine ribonucleosides and guanine nucleotides are readily functionalized with CF3 substituents within the nucleobase. Protected guanosine is trifluoromethylated at the C8 position under radical-generating conditions in up to 95% yield and guanosine 5′-oligophosphates in up to 35% yield. In the case of adenosine, the selectivity of trifluoromethylation depends heavily on the functional group protection strategy and leads to a set of CF3-modified nucleosides with different substitution patterns (C8, C2, or both) in up to 37% yield. Further transformations based on phosphorimidazolide chemistry afford various CF3-substituted mono- and dinucleoside oligophosphates in good yields. The utility of the trifluoromethylated nucleotides as probes for 19F NMR-based real-time enzymatic reaction monitoring is demonstrated with three different human nucleotide hydrolases (Fhit, DcpS, and cNIIIB). Substrate and product(s) resonances were sufficiently separated to enable effective tracking of each enzymatic activity of interest.
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Gough,Maguire
, p. 866 (1965)
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Novel, Stable Congeners of the Antiretroviral Compound 2',3'-Dideoxyadenosine
Nair, Vasu,Buenger, Greg S.
, p. 8502 - 8504 (2007/10/02)
Novel congeners of the antiretroviral compound 2',3'-dideoxyadenosine (ddA) have been synthesized through metal-mediated and photochemical conversions as the key steps.These compounds are inherently more stable than ddA with respect to both glycosidic bond cleavage and deamination by adenosine deaminase.
