Molecules (Nov 2017)

Synthesis of Spironucleosides: Past and Future Perspectives

  • Raquel G. Soengas,
  • Gustavo da Silva,
  • Juan Carlos Estévez

DOI
https://doi.org/10.3390/molecules22112028
Journal volume & issue
Vol. 22, no. 11
p. 2028

Abstract

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Spironucleosides are a type of conformationally restricted nucleoside analogs in which the anomeric carbon belongs simultaneously to the sugar moiety and to the base unit. This locks the nucleic base in a specific orientation around the N-glycosidic bond, imposing restrictions on the flexibility of the sugar moiety. Anomeric spiro-functionalized nucleosides have gained considerable importance with the discovery of hydantocidin, a natural spironucleoside isolated from fermentation broths of Streptomyces hygroscopicus which exhibits potent herbicidal activity. The biological activity of hydantocidin has prompted considerable synthetic interest in this nucleoside and also in a variety of analogues, since important pharmaceutical leads can be found among modified nucleoside analogues. We present here an overview of the most important advances in the synthesis of spironucleosides.

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