Chemical Synthesis of Nucleoside Analogues

Chemical Synthesis of Nucleoside Analogues

Editor(s): Pedro Merino

Published Online: 15 FEB 2013 10:56AM EST

Print ISBN: 9781118007518

Online ISBN: 9781118498088

DOI: 10.1002/9781118498088

About this Book

Compiles current tested and proven approaches to synthesize novel 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.

Table of contents

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    3. Chapter 3

      Chemical Synthesis of Acyclic Nucleosides (pages 103–162)

      Hai-Ming Guo, Shan Wu, Hong-Ying Niu, Ge Song and Gui-Rong Qu

    4. Chapter 4

      Phosphonated Nucleoside Analogues (pages 163–208)

      Roberto Romeo, Caterina Carnovale, Antonio Rescifina and Maria Assunta Chiacchio

    5. Chapter 7

      Synthesis of C-Nucleosides (pages 263–316)

      Omar Boutureira, M. Isabel Matheu, Yolanda Díaz and Sergio Castillón

    6. Chapter 9

      Synthesis of Conformationally Constrained Nucleoside Analogues (pages 345–426)

      Esma Maougal, Jean-Marc Escudier, Christophe Len, Didier Dubreuil and Jacques Lebreton

    7. Chapter 11

      L-Nucleosides (pages 473–534)

      Daniela Perrone and Massimo L. Capobianco

    8. Chapter 17

      Isoxazolidinyl Nucleosides (pages 781–818)

      Ugo Chiacchio, Antonino Corsaro, Salvatore Giofrè and Giovanni Romeo

    9. You have free access to this content