Advances in the Synthesis of Spirocyclic Nucleosides

Sumit Kumar; Yousuf Khan; Aditi Arora; Manish Kumar; Pallavi Rungta; Brajendra K. Singh; Vivek K. Sharma; Sunil K. Singh

doi:10.1055/s-0042-1751509

Synthesis, Table of Contents

Synthesis 2024; 56(07): 1097-1138
DOI: 10.1055/s-0042-1751509

short review

Emerging Trends in Glycoscience

Advances in the Synthesis of Spirocyclic Nucleosides

Sumit Kumar‡

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110007, India

,

Yousuf Khan‡

^bDepartment of Chemistry, Kirori Mal College, University of Delhi, Delhi-110007, India

^cNational Centre of Competence in Research (NCCR) Chemical Biology, University of Geneva, Geneva, 1211, Switzerland

,

Aditi Arora‡

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110007, India

,

Manish Kumar

^dDepartment of Chemistry, Moti Lal Nehru College, University of Delhi, Delhi-110007, India

,

Pallavi Rungta

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110007, India

,

Brajendra K. Singh

^aBioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi-110007, India

,

Vivek K. Sharma∗

^eDepartment of Medicine, Mass Biologics of the University of Massachusetts Chan Medical School, Mattapan, MA 02126, USA

,

Sunil K. Singh∗

^bDepartment of Chemistry, Kirori Mal College, University of Delhi, Delhi-110007, India

› Author Affiliations

Abstract

All articles of this category

Dedicated to Late Professor Ashok K. Prasad, Department of Chemistry, University of Delhi, India.

Abstract

The nucleosides are the building blocks for nucleic acids and composed of a five-carbon sugar bearing either pyrimidine or purine nucleobase. The biological properties of nucleosides can be tailored by chemically modifying the five-carbon sugar to influence its sugar pucker. The spirocyclic scaffold is an indispensable scaffold in more than ten approved drugs, and its inherent three-dimensionality makes it an ideal modification to influence the sugar pucker and biological properties of nucleosides. However, the introduction of spirocyclic scaffold is often synthetically challenging due to increase in synthetic steps and stereocenters. The present review highlights the advances in synthetic methodologies developed during the past decades for accessing various members of the spiro-functionalized nucleoside family.

1 Introduction

2 C-1′-Spirocyclic Nucleosides

3 C-2′-Spirocyclic Nucleosides

4 C-3′-Spirocyclic Nucleosides

5 C-4′-Spirocyclic Nucleosides

6 Miscellaneous Spirocyclic Nucleosides

7 Conclusion and Future Perspectives

Key words

sugar-modified nucleoside - hydantocidin - spironucleoside - spirocyclic scaffold - Vorbrüggen glycosylation - chemoenzymatic synthesis

Full Text

References

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