Recent developments in the chemistry of nucleosides

Jean-Luc Girardet and Stanley A. Lang Valeant Research Development, 

3300 Hyland Avenue, Costa Mesa, CA 92626 jlgirardet valeant.com, salang valeant.com 

This chapter will review the recent developments in nucleoside research both in term of chemistry and potential medical use. We will first review modifications brought to the ribose or 2 -deoxyribose moiety of a nucleoside, from C-1 to C-5 (nucleoside nomenclature). We will then look at publications on ribose replacement with unnatural sugars, including carba, thia and aza sugars, and then we will review the literature on bicyclonucleosides published in recent years. This chapter will be concluded with a review of recent articles on nucleoside synthesis on solid support, and the challenges associated with this technique applied to nucleoside synthesis. 

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A brief review on keto derivatives of aldohexosyl nucleosides appeared16 in 1975, and a plenary lecture entitled Recent Developments in the Chemistry of Ketonucleosides has been given.17... 

The synthesis and chemistry of heterocyclic analogues of purine nucleosides and nucleotides have been comprehensively reviewed, as have the synthesis and properties of various disaccharide nucleosides.5 Other reviews have discussed the importance of nucleoside analogues in chemotherapy and in other potential therapeutic applications such as immunomodulation or the regulation of gene expression, recent developments in the synthesis of nucleoside analogues with anti-HIV activity, and the synthesis of 2, 3 -dideoxynucleosides, with or widiout substituents at C-2 or C-3, by methods which involve condensations of modified sugars with heterocyclic bases. In a review on progress in free radical chemistry in his laboratories. Barton has discussed applications to the synthesis of C-nucleosides, chain-extended nucleosides and nucleoside phosphonates. ... 

Current progress in the chemistry of nucleoside antibiotics and recent developments in the synthesis of anti-HIV dideoxy nucleosides have been reviewed. A further review on the use of radical reactions for synthesizing nucleosides including antibiotics is mentioned in Chapter 20. 

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