Chemical Synthesis of Nucleoside Analogues (eBook)

Pedro Merino (Herausgeber)

eBook Download: PDF

2013 | 1. Auflage
912 Seiten
John Wiley & Sons (Verlag)
978-1-118-49817-0 (ISBN)

Infos

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.

Autor

PEDRO MERINO, PhD, is the Director of the Department of Synthesis and Structure of Biomolecules of the Institute of Chemical Synthesis and Homogenous Catalysis at the University of Zaragoza. Dr. Merino has authored more than 200 publications, including several reviews and book chapters. His research spans asymmetric synthesis, target-oriented synthesis, organometallic chemistry, and asymmetric metal-assisted and organic catalysis. Recently, he has been investigating the use of computational chemistry to better understand reaction mechanisms.

Inhalt

Contributors ix

Foreword xiii

Preface xv

1 Biocatalytic Methodologies for Selective Modified Nucleosides
1

Miguel Ferrero, Susana Fern´andez, and Vicente
Gotor

2 Nucleosides Modified at the Base Moiety 49

O. Sari, V. Roy, and L. A. Agrofoglio

3 Chemical Synthesis of Acyclic Nucleosides 103

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

4 Phosphonated Nucleoside Analogues 163

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

5 Chemical Syntheses of Nucleoside Triphosphates 209

Lina Weinschenk and Chris Meier

6 Mononucleotide Prodrug Synthetic Strategies 229

Suzanne Peyrottes and Christian P´erigaud

7 Synthesis of C-Nucleosides 263

Omar Boutureira, M. Isabel Matheu, Yolanda D´yaz, and
Sergio Castill´on

8 Methodologies for the Synthesis of Isomeric Nucleosides and
Nucleotides of Antiviral Significance 317

Maurice Okello and Vasu Nair

9 Synthesis of Conformationally Constrained Nucleoside Analogues
345

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

10 Synthesis of 3-Spiro-Substituted Nucleosides: Chemistry of
TSAO Nucleoside Derivatives 427

Mar´ya-Jos´e Camarasa, Sonsoles Vel´azquez,
Ana San-F´elix, and Mar´ya-Jes´us
P´erez-P´erez

11 l-Nucleosides 473

Daniela Perrone and Massimo L. Capobianco

12 Chemical Synthesis of Carbocyclic Analogues of Nucleosides
535

E. Leclerc

13 Uncommon Three-, Four-, and Six-Membered Nucleosides
605

E. Groaz and P. Herdewijn

14 Recent Advances in Synthesis and Biological Activity of
4-Thionucleosides 655

Varughese A. Mulamoottil, Mahesh S. Majik, Girish Chandra, and
Lak Shin Jeong

15 Recent Advances in the Chemical Synthesis of Aza-Nucleosides
699

Tom´as Tejero, Ignacio Delso, and Pedro Merino

16 Stereoselective Methods in the Synthesis of Bioactive
Oxathiolane and Dioxolane Nucleosides 727

D. D'Alonzo and A. Guaragna

17 Isoxazolidinyl Nucleosides 781

Ugo Chiacchio, Antonino Corsaro, Salvatore Giofr`e, and Giovanni
Romeo

18 Synthetic Studies on Antifungal Peptidyl Nucleoside
Antibiotics 819

Apurba Datta

19 Chemical Synthesis of Conformationally Constrained PNA
Monomers 847

Pedro Merino and Rosa Matute

Index 881

Produkt-Details

• Erscheint lt. Verlag: 12.2.2013
• Sprache: englisch
• Themenwelt: Medizin / Pharmazie ► Gesundheitsfachberufe
• Themenwelt: Medizin / Pharmazie ► Medizinische Fachgebiete ► Pharmakologie / Pharmakotherapie
• Themenwelt: Naturwissenschaften ► Biologie ► Biochemie
• Themenwelt: Naturwissenschaften ► Biologie ► Genetik / Molekularbiologie
• Themenwelt: Naturwissenschaften ► Chemie ► Organische Chemie
• Themenwelt: Technik
• Schlagworte: Biochemie u. Chemische Biologie • Biochemistry (Chemical Biology) • bioorganic chemistry • bioorganische Chemie • Chemie • Chemische Synthese • Chemistry • Methods - Synthesis & Techniques • Nukleoside • Organische Chemie / Methoden, Synthesen, Verfahren
• ISBN-10: 1-118-49817-8 / 1118498178
• ISBN-13: 978-1-118-49817-0 / 9781118498170