Synthesis of Spironucleosides: Past and Future Perspectives

Autor: Raquel G. Soengas, Gustavo da Silva, Juan Carlos Estévez
Jazyk: angličtina
Rok vydání: 2017
Předmět:
Zdroj: Molecules, Vol 22, Iss 11, p 2028 (2017)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules22112028
Popis: 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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