Chemical Synthesis of Nucleoside Analogues: Merino/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. Content: Chapter 1 Biocatalytic Methodologies for Selective Modified Nucleosides (pages 1–48): Miguel Ferrero, Susana Fernandez and Vicente Gotor Chapter 2 Nucleosides Modified at the Base Moiety (pages 49–101): O. Sari, V. Roy and L. A. Agrofoglio Chapter 3 Chemical Synthesis of Acyclic Nucleosides (pages 103–162): Hai?Ming Guo, Shan Wu, Hong?Ying Niu, Ge Song and Gui?Rong Qu Chapter 4 Phosphonated Nucleoside Analogues (pages 163–208): Roberto Romeo, Caterina Carnovale, Antonio Rescifina and Maria Assunta Chiacchio Chapter 5 Chemical Syntheses of Nucleoside Triphosphates (pages 209–227): Lina Weinschenk and Chris Meier Chapter 6 Mononucleotide Prodrug Synthetic Strategies (pages 229–261): Suzanne Peyrottes and Christian Perigaud Chapter 7 Synthesis of C?Nucleosides (pages 263–316): Omar Boutureira, M. Isabel Matheu, Yolanda Diaz and Sergio Castillon Chapter 8 Methodologies for the Synthesis of Isomeric Nucleosides and Nucleotides of Antiviral Significance (pages 317–343): Maurice Okello and Vasu Nair Chapter 9 Synthesis of Conformationally Constrained Nucleoside Analogues (pages 345–426): Esma Maougal, Jean?Marc Escudier, Christophe Len, Didier Dubreuil and Jacques Lebreton Chapter 10 Synthesis of 3??Spiro?Substituted Nucleosides: Chemistry of TSAO Nucleoside Derivatives (pages 427–472): Maria?Jose Camarasa, Sonsoles Velazquez, Ana San?Felix and Maria?Jesus Perez?Perez Chapter 11 L?Nucleosides (pages 473–534): Daniela Perrone and Massimo L. Capobianco Chapter 12 Chemical Synthesis of Carbocyclic Analogues of Nucleosides (pages 535–604): E. Leclerc Chapter 13 Uncommon Three?, Four?, and Six?Membered Nucleosides (pages 605–654): E. Groaz and P. Herdewijn Chapter 14 Recent Advances in Synthesis and Biological Activity of 4??Thionucleosides (pages 655–697): Varughese A. Mulamoottil, Mahesh S. Majik, Girish Chandra and Lak Shin Jeong Chapter 15 Recent Advances in the Chemical Synthesis of Aza?Nucleosides (pages 699–725): Tomas Tejero, Ignacio Delso and Pedro Merino Chapter 16 Stereoselective Methods in the Synthesis of Bioactive Oxathiolane and Dioxolane Nucleosides (pages 727–780): D. D'alonzo and A. Guaragna Chapter 17 Isoxazolidinyl Nucleosides (pages 781–818): Ugo Chiacchio, Antonino Corsaro, Salvatore Giofre and Giovanni Romeo Chapter 18 Synthetic Studies on Antifungal Peptidyl Nucleoside Antibiotics (pages 819–846): Apurba Datta Chapter 19 Chemical Synthesis of Conformationally Constrained PNA Monomers (pages 847–880): Pedro Merino and Rosa Matute 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. Content: Chapter 1 Biocatalytic Methodologies for Selective Modified Nucleosides (pages 1–48): Miguel Ferrero, Susana Fernandez and Vicente GotorChapter 2 Nucleosides Modified at the Base Moiety (pages 49–101): O. Sari, V. Roy and L. A. AgrofoglioChapter 3 Chemical Synthesis of Acyclic Nucleosides (pages 103–162): Hai?Ming Guo, Shan Wu, Hong?Ying Niu, Ge Song and Gui?Rong QuChapter 4 Phosphonated Nucleoside Analogues (pages 163–208): Roberto Romeo, Caterina Carnovale, Antonio Rescifina and Maria Assunta ChiacchioChapter 5 Chemical Syntheses of Nucleoside Triphosphates (pages 209–227): Lina Weinschenk and Chris MeierChapter 6 Mononucleotide Prodrug Synthetic Strategies (pages 229–261): Suzanne Peyrottes and Christian PerigaudChapter 7 Synthesis of C?Nucleosides (pages 263–316): Omar Boutureira, M. Isabel Matheu, Yolanda Diaz and Sergio CastillonChapter 8 Methodologies for the Synthesis of Isomeric Nucleosides and Nucleotides of Antiviral Significance (pages 317–343): Maurice Okello and Vasu NairChapter 9 Synthesis of Conformationally Constrained Nucleoside Analogues (pages 345–426): Esma Maougal, Jean?Marc Escudier, Christophe Len, Didier Dubreuil and Jacques LebretonChapter 10 Synthesis of 3??Spiro?Substituted Nucleosides: Chemistry of TSAO Nucleoside Derivatives (pages 427–472): Maria?Jose Camarasa, Sonsoles Velazquez, Ana San?Felix and Maria?Jesus Perez?PerezChapter 11 L?Nucleosides (pages 473–534): Daniela Perrone and Massimo L. CapobiancoChapter 12 Chemical Synthesis of Carbocyclic Analogues of Nucleosides (pages 535–604): E. LeclercChapter 13 Uncommon Three?, Four?, and Six?Membered Nucleosides (pages 605–654): E. Groaz and P. HerdewijnChapter 14 Recent Advances in Synthesis and Biological Activity of 4??Thionucleosides (pages 655–697): Varughese A. Mulamoottil, Mahesh S. Majik, Girish Chandra and Lak Shin JeongChapter 15 Recent Advances in the Chemical Synthesis of Aza?Nucleosides (pages 699–725): Tomas Tejero, Ignacio Delso and Pedro MerinoChapter 16 Stereoselective Methods in the Synthesis of Bioactive Oxathiolane and Dioxolane Nucleosides (pages 727–780): D. D'alonzo and A. GuaragnaChapter 17 Isoxazolidinyl Nucleosides (pages 781–818): Ugo Chiacchio, Antonino Corsaro, Salvatore Giofre and Giovanni RomeoChapter 18 Synthetic Studies on Antifungal Peptidyl Nucleoside Antibiotics (pages 819–846): Apurba DattaChapter 19 Chemical Synthesis of Conformationally Constrained PNA Monomers (pages 847–880): Pedro Merino and Rosa Matute

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.

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. Deoxynucleoside analogues / Vicente Gotor Nucleosides modified at the base moiety / Luigi Agrofoglio Acyclic nucleosides / Antonin Holy Phosphorylated nucleoside analogues / Giovanni Romeo Triphosphorylated nucleoside analogues / Chris Meier Pro-nucleotides / Christian Perigaud C-nucleoside / Sergio Castillón Isonucleosides / Vasu Nair Conformationally constrained nucleosides / Jacques Lebreton Spironucleosides / Maria Jose Camarasa L-nucleosides / Daniela Perrone Carbocyclic nucleosides / Eric Leclerc Uncommon three-, four, and six-membered nucleosides / Elisabetta Groaz Thionucleosides / L.S. Jeong Azanucleosides and related compounds / Tomas Tejero Oxathiolane and dioxolane nucleosides / Annalisa Guaragna Isoxazolidinyl nucleosides / Ugo Chiacchio Nucleoside antibiotics / Apurba Dutta Building blocks for peptide nucleic acids / Pedro Merino.