Journal
MOLECULES
Volume 22, Issue 11, Pages -Publisher
MDPI
DOI: 10.3390/molecules22112028
Keywords
spironucleosides; spirohydantoins; spirodiketopiperazines; sugar amino acids
Funding
- Xunta de Galicia (Centro singular de investigacion de Galicia accreditation)
- European Union (European Regional Development Fund-ERDF)
- FCT [SFRH/BD/103412/2014]
- Fundação para a Ciência e a Tecnologia [SFRH/BD/103412/2014] Funding Source: FCT
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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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