Chemical Synthesis of Nucleoside Analogues

Featuring contributions from leading synthetic chemists from around the world, this book brings together and describes tested and proven approaches for the chemical synthesis of common families of nucleoside analogues. Readers will learn to create new nucleoside analogues with desired therapeutic properties by using a variety of methods to chemically modify natural nucleosides, including:

• Changes to the heterocyclic base
• Modification of substituents at the sugar ring
• Replacement of the furanose ring by a different carbo- or heterocyclic ring
• Introduction of conformational restrictions
• Synthesis of enantiomers
• Preparation of hydrolitically stable C-nucleosides

Chemical Synthesis of Nucleoside Analogues covers all the major classes of nucleosides, including pronucleotides, C-nucleosides, carbanucleosides, and PNA monomers which have shown great promise as starting points for the synthesis of nucleoside analogues. The book also includes experimental procedures for key reactions related to the synthesis of nucleoside analogues, providing a valuable tool for the preparation of a number of different compounds.

Throughout the book, chemical schemes and figures help readers better understand the chemical structures of nucleoside analogues and the methods used to synthesize them. Extensive references serve as a gateway to the growing body of original research studies and reviews in the field.

Synthetically modified nucleosides have proven their value as therapeutic drugs, in particular as antiviral and antitumor agents. However, many of these nucleoside analogues have undesirable side effects. With Chemical Synthesis of Nucleoside Analogues as their guide, researchers have a new tool for synthesizing a new generation of nucleoside analogues that can be used as therapeutic drugs with fewer unwanted side effects.

Preface

Contributors

1. Deoxynucleoside analogues (50 pp)
Prof. Vicente Gotor, University of Oviedo. Spain

2. Nucleosides modified at the base moiety (50 pp)
Prof. Luigi Agrofoglio, University of Orleans. France

3. Acyclic Nucleosides (50 pp)
Prof. Antonin Holy, Academy of Sciences of the Czech Republic

4. Phosphorylated nucleoside analogues (40 pp)
Prof. Giovanni Romeo, University of Messina. Italy

5. Triphosphorylated nucleoside analogues (20 pp)
Prof. Chris Meier, University of Hamburg. Germany

6. Pro-nucleotides (30 pp)
Prof. Christian Perigaud, University of Montpellier 2. France

7. C-Nucleosides (50 pp)
Prof. Sergio Castillón, University Rovira i Virgili. Spain

8. Isonucleosides (30 pp)
Prof. Vasu Nair, University of Georgia. USA

9. Conformationally constrained nucleosides (40 pp)
Prof. Jacques Lebreton, University of Nantes. France

10. Spironucleosides (30 pp)
Prof. Maria Jose Camarasa, Spanish Council of Scientific Research. Spain

11. L-nucleosides (30 pp)
Dr. Daniela Perrone, University of Ferrara. Italy

12. Carbocyclic Nucleosides (60 pp)
Dr. Eric Leclerc, University of Rouen. France

13. Uncommon three-, four and six-membered nucleosides (40 pp)
Dr.  Elisabetta Groaz, University of Leuven. Belgium

14. Thionucleosides (25 pp)
Prof. L. S. Jeong, Ewha University. South Korea

15. Azanucleosides and related compounds (40 pp)
Prof. Tomas Tejero, University of Zaragoza. Spain

16. Oxathiolane and dioxolane nucleosides (30 pp)
Dr. Annalisa Guaragna, University of Napoli. Italy

17. Isoxazolidinyl nucleosides (30 pp)
Prof. Ugo Chiacchio, University of Catania. Italy

18. Nucleoside antibiotics (40 pp)
Prof. Apurba Dutta, University of Kansas. USA

19. Building blocks for peptide nucleic acids (30 pp)
Prof. Pedro Merino, University of Zaragoza. Spain

Index