Targeting of ribonucleotide reductase with 2'-Disulfide analogs of adenosine. Electronic versus steric effects in radical deoxygenation of fluorine-containing nucleosides

Abstract

Companioni, Dania, "Targeting of ribonucleotide reductase with 2'-Disulfide analogs of adenosine. Electronic versus steric effects in radical deoxygenation of fluorine-containing nucleosides" (2002 Fluorinated compounds are widely used in biochemistry, medicinal chemistry, and pharmacology. Synthesis of '-deoxy-'-fluoroadenosine and its arabino epimer as well as 3-deoxy-3'-fluoroadenosine and its xylo epimer were also targeted in order to study the electronic versus steric P-fluorine effects in radical deoxygenation of fluorine containing pentofuranose nucleosides. Our results clearly show that steric effect o f the heterocyclic base from the 3-face of the sugar is decisive, favoring the incorporation of deuterium from the less hindered c-face.