Chemistry of Nucleosides and Nucleotides: Volume 1

ISBN-13: 9781461282839 / Angielski / Miękka / 2011 / 404 str.

L. B. Townsend

Opis

The present volume is the first of a projected four-volume treatise. This volume contains the following chapters: "Synthesis and Reaction of Pyrimidine Nucleosides," "Synthesis and Properties of Purine Nucleosides and Nucleotides," and "Synthesis and Properties of Oligonucleotides." These three chapters were selected for inclusion in Volume I because the areas have provided the basis and impetus for the initiation and development of the other areas of research, which will be described in subsequent volumes. Each chapter is rather comprehensive in nature and should provide a ready reference source for not only the novice but also the experienced investigator or researcher. The chapters have been prepared by authors with considerable experience in each particular area of research, and this has resulted in a lucid presentation of each well-defined area. These volumes were designed with medicinal chemists, medicinal organic chemists, organic chemists, carbohydrate chemists, physical chemists, and biological chemists in mind. However, because of the tremendous recent interest in this research area owing to the biological and chemotherapeutic evaluation of nucleosides and nucleotides as anticancer, antiviral, and antiparasitic agents, these volumes should also be valuable additions to the libraries of virologists, biochemical pharmacologists, oncologists, and pharmacologists. We would like to thank the authors for their enthusiasm and help in making these volumes available to the scientific community.

Spis treści

1 Synthesis and Reaction of Pyrimidine Nucleosides.- 1. Introduction.- 2. Synthesis of Pyrimidine Nucleosides.- 2.1. The Vorbrüggen Method.- 2.2. The Mercuri Procedure.- 2.3. Ring Closure of N-Substituted Ribosylamines.- 3. Reaction of Pyrimidine Nucleosides in the Heterocyclic Moiety.- 3.1. Protonation.- 3.2. Alkylation and Related Reactions.- 3.3. N-Oxidation and N-Amination.- 3.4. Nitration.- 3.5. Hydroxymethylation and Related Reactions.- 3.6. Halogenation.- 3.7. Mercuration, Metallation, and Related Reactions.- 3.8. Nucleophilic Additions.- 3.9. Reactions of 5-Halogenopyrimidine Nucleosides with Nucleophiles and Related Reactions.- 3.10. Substitution at C-4 and C-2 and Related Reactions.- 3.11. Oxidations.- 3.12. Reductions.- 4. Synthesis and Reactions of Cyclonucleosides.- 4.1. Synthesis of Cyclonucleosides.- 4.2. Reaction of Cyclonucleosides.- 4.3. Cyclonucleosides Bridged by Sulfur and Nitrogen.- 4.4. Cyclonucleosides Bridged by Carbon.- 5. Reactions of Pyrimidine Nucleosides in the Sugar Moiety.- 5.1. Alkylation of Sugar Hydroxyl Groups.- 5.2. Conversion of Sugar Hydroxyls to Halogeno Groups.- 5.3. Conversion of 5? and (3?)-Hydroxyl Groups to Other Functional Groups.- 5.4. Epoxides of Pyrimidine Nucleosides.- 5.5. Introduction of Double Bonds in the Sugar Moiety.- 5.6. Oxidation of the Sugar Moiety.- 6. Reactions Involving Cleavage of Glycosyl Bond and Anomerization.- 7. References.- 2 Synthesis and Properties of Purine Nucleosides and Nucleotides.- 1. Introduction.- 2. Synthesis of Purine Nucleosides and Nucleotides.- 2.1. Direct Glycosylation of Purines.- 2.2. Synthesis of Purine Nucleosides and Nucleotides from Imidazole and Pyrimidine Nucleosides and Nucleotides.- 2.3. Phosphorylation of Purine Nucleosides.- 2.4. Synthesis of Purine Nucleoside Cyclic Phosphates.- 3. Reactions of Purine Nucleosides and Nucleotides.- 3.1. Reactions of the Carbohydrate Portion of Purine Nucleosides and Nucleotides.- 3.2. Reactions of the Purine Ring of Purine Nucleosides and Nucleotides.- 3.3. Interaction of the Sugar and the Purine Ring: Purine Cyclonucleosides.- 3.4. Hydrolysis of the Glycosyl Bond: Stabilities and Mechanism.- 4. References.- 3 Synthesis and Properties of Oligonucleotides.- 1. Introduction.- 2. Protecting Groups and Phosphorylation Methods.- 2.1. Protecting Groups for Bases.- 2.2. Protecting Groups for Sugar Hydroxyl Groups.- 2.3. Protecting Groups for Phosphates and Phosphorylating Reagents.- 2.4. Condensing Reagents.- 3. Synthesis of Oligonucleotides by the Phosphotriester Method.- 3.1. Synthesis of Oligo(deoxyribonucleotides) in Solution.- 3.2. Synthesis of Oligo(deoxyribonucleotides) on Polymer Supports.- 3.3. Synthesis of Oligo(ribonucleotides) in Solution.- 3.4. Synthesis of Oligo(ribonucleosides) on Polymer Supports.- 4. Phosphite Method.- 4.1. Synthesis of Oligo(deoxyribonucleotides) in Solution.- 4.2. Synthesis of Oligo(deoxyribonucleotides) on Polymer Supports.- 4.3. Synthesis of Oligo(ribonucleotides) in Solution.- 4.4. Synthesis of Oligo(ribonucleotides) on Polymer Support.- 4.5. Synthesis of Modified Nucleotides.- 5. Purification and Characterization of Oligonucleotides.- 5.1. Isolation of Oligonucleotides.- 5.2. Identification of Oligonucleotides.- 6. Joining Reactions and Other Usage of Synthetic Oligonucleotides.- 6.1. Synthesis of Genes by Joining of Deoxyoligonucleotides with DNA Ligase.- 6.2. Use of Oligonucleotides as Probes or Primers for Sequencing DNA.- 6.3. Use of Deoxyoligonucleotides on Site-Directed Mutagenesis.- 6.4. Joining of Ribo-oligonucleotides with RNA Ligase.- 7. Structure and Properties of Oligonucleotides.- 7.1. Crystal Structure of Oligonucleotides.- 7.2. Conformation of Oligonucleotides in Solution.- 7.3. Interaction of Oligonucleotides with Drugs.- 7.4. Reactions of Oligonucleotides with Drugs.- 8. References.