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Molecules 2017, 22(11), 2028; doi:10.3390/molecules22112028

Synthesis of Spironucleosides: Past and Future Perspectives

1
Organic Chemistry Area, University of Almeria, Carretera de Sacramento s/n, 04120 Almería, Spain
2
Research Institute for Medicines (iMed.ULisboa), Faculty of Pharmacy, Universidade de Lisboa, 1649-003 Lisbon, Portugal
3
Research Center in Biological Chemistry and Molecular Materials (CIQUS) and Organic Chemistry Department, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain
*
Authors to whom correspondence should be addressed.
Received: 16 October 2017 / Revised: 17 November 2017 / Accepted: 19 November 2017 / Published: 22 November 2017
(This article belongs to the Special Issue Advances in Spiro Compounds)

Abstract

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. View Full-Text
Keywords: spironucleosides; spirohydantoins; spirodiketopiperazines; sugar amino acids spironucleosides; spirohydantoins; spirodiketopiperazines; sugar amino acids
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Soengas, R.G.; da Silva, G.; Estévez, J.C. Synthesis of Spironucleosides: Past and Future Perspectives. Molecules 2017, 22, 2028.

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