Abstract
The original underlying concept for the synthesis of carbocyclic nucleosides has been to seek a stable C–N bond to replace the hydrolytically and enzymatically scissile glycosylic bond, while causing minimal structural disturbances. The activities of most conventional carbocyclic nucleosides have been poorer than the corresponding ribosides. The replacement of the ring oxygen is symbolized by the term “ carba ,” which is also used as a prefix when referring to carbocyclic nucleoside analogs of traditional compounds. Carba -nucleosides include carbocyclic nucleosides containing a saturated cyclopentane ring with substituents on the pseudofuranose ring except fluorine. This chapter describes carbocyclic nucleosides containing a saturated cyclopentane ring with substituents on the pseudofuranose ring except fluorine. The absence of the 4' oxygen in carba -nucleosides represents a dramatic change in terms of stereoelectronic effects. Neplanocin A is the paradigm among the broad-spectrum antiviral agents that function as the inhibitors of S-AdoHcy-ase. The correlation between the inhibitory capacity of this enzyme, and the ensuing antiviral activity, particularly against negative-stranded RNA viruses, has been well established.
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