Work

Efficient Syntheses of 5‘-Deoxy-5‘-fluoroguanosine and -inosine

Year: 2007

Type: article

Abstract: Substitution of oxygen with a weak hydrogen bond acceptor such as fluorine provides a single-atom modification that can have grave effects on the chemical and medicinal properties of nucleoside analogues. To that end, we present a simple and high-yielding method for the novel synthesis of 5'-deoxy-5'-fluoroguanosine and 5'-deoxy-5'-fluoroinosine utilizing an intramolecular electron-withdrawing approach. The properties of the resulting modified nucleosides, as well as the halogenated intermediates, are notable for their similarity to nucleoside analogues used in the treatment of cancer, as well as enzyme inhibitors designed to target parasitic protozoa.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo7015778

Authors: Robert C. Spitale, Moriah G. Heller, Amanda J. Pelly, Joseph E. Wedekind

Institutions: University of Rochester Medicine, University of Rochester

Language: English

Topic: Fluorine in Organic Chemistry

Subfield: Pharmaceutical Science

Field: Pharmacology, Toxicology and Pharmaceutics

Domain: Life Sciences

Open Access status: green

Funders: National Science Foundation, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry

Awards: G2403216270, G2710299537, Mechanisms of Action On Non-Coding RNA Molecules, Purchase of a High Resolution Mass Spectrometer with HPLC for Shared Use, G9000025309