Perspectives in Nucleoside and Nucleic Acid Chemistry

The chemistry of nucleosides and nucleic acids is a rapidly developing field. Many of the most important recent advances in medicinal chemistry have occured in this field with the development of novel nucleoside- and nucleotide-based antiviral and antitumor drugs. New synthesis strategies involving novel protecting groups have helped spur progress in drug-development and genome-sequencing research. This volume, comprised of contributions written by internationally recognized experts, covers cutting-edge developments in current nucleoside and nucleic acid research. The most recent synthesis innovations, including combinatorial approaches, spectroscopy and structural studies, thermodynamic and computational investigations, stability assessments, and medicinal applications are presented. Synthetic, physical, organic, bioorganic, and medicinal chemists working on all aspects of nucleoside and nucleic acid research will value this comprehensive state-of-the-art overview.

Table of Contents:
NUCLEOSIDES AND NUCLEOTIDES. The Synthesis of Bicyclic N 4 --Amino--2'--deoxycytidine Derivatives (D Loakes, et al.). Synthesis and Biological Activity of 2'--Fluoro--D--arabinofuranosylpyrazolo-- [3,4--d]pyrimidine Nucleosides (A. Shortnacy--Fowler, et al.). A Novel Route for the Synthesis of Deoxy Fluoro Sugars and Nucleosides (I. Mikhailopulo & G. Sivets). A Practical Synthesis of 3'--Thioguanosine and of Its 3'--Phosphoramidothioite (a Thiophosphoramidite) (J. Matulic--Adamic & L. Beigelman). Novel Nucleoside Analogues with Fluorophores Replacing the DNA Base (C. Strassler, et al.). 2--(Glucosylthio)ethyl Groups as Potential Biolabile Phosphate--Protecting Groups of Mononucleotides (N. Schlienger, et al.). New 2--(4--Nitrophenyl)ethyl(Npe)-- and 2--(4--Nitrophenyl)ethoxycarbonyl--(Npeoc)--Protected 2'--Deoxyribonucleosides and Their 3'--Phosphoramidites -- Versatile Building Blocks for Oligonucleotide Synthesis (H. Lang, et al.). Synthesis of Conformationally Restricted Carbocyclic Nucleosides: The Role of the O(4')--Atom in the Key Hydration Step of Adenosine Deaminase (V. Marquez, et al.). Studies on the Adamantylation of N--Heterocycles and Nucleosides (Z. Kazimierczuk, et al.). Six--Membered Carbocyclic Nucleosides with a Purine Base Moiety: Synthesis, Conformational Analysis, and Antiviral Activity (J. Wang & P. Herdewijn). Individual Isomers of Dinucleoside Boranophosphates as Synthons for Incorporation into Oligonucleotides: Synthesis and Configurational Assignment (Z. Sergueeva, et al.). Synthesis of Boron--Containing ADP and GDP Analogues: Nucleoside 5'--(P alpha --Boranodiphosphates) (J. Lin, et al.). Isonucleosides with Exocyclic Methylene Groups (S. Bera & V. Nair). OLIGONUCLEOTIDES. Oligonucleotides Fuctionalized by Fluorescein and Rhodamine Dyes: Michael Addition of Methyl Acrylate to 2'--Deoxypseudouridine (N. Ramzaeva, et al.). Base--Pairing Properties of 8--Aza--7--deazaadenine Linked via the 8--Position to the DNA Backbone (F. Seela, et al.). Nucleic--Acid Analogs with Restricted Conformational Flexibility in the Sugar-- Phosphate Backbone ('Bicyclo--DNA'). Part 7. Synthesis and Properties of Oligodeoxynucleotides Containing [(3'S,5'S,6'R)--6'--Amino--2'--deoxy--3',5'-- ethano--beta--D--ribofuranosyl]thymine ( = (6'R)--6'--Amino--bicyclo--thymidine) (R. Meier, et al.). Oligonucleotides Containing Novel 4'--C-- or 3'--C--(Aminoalkyl)--Branched Thymidines (H. Pfundheller, et al.). 1H'--Benzotriazole as Synthetic Auxiliary in a Facile Route to N 6 --(Arylmethyl)-- 2'--deoxyadenosines: DNA Intercalators Inserted into Three--Way Junctions (S. El--Kafrawy, et al.). Dipyrido[3,2--a:2',3'--c]phenazine--Tethered Oligo--DNA Synthesis and Thermal Stability of Their DNA DNA and DNA RNA Duplexes and DNA DNA DNA Triplexes (D. Ossipov, et al.). Synthesis and Properties of Oligothymidylates Incorporating an Artificial Bend Motif (K. Seio, et al.). Synthesis of the Anticodon Hairpin 'RNA f Met Containing N--{[9--(beta--D-- Ribofuranosyl)--9H--purin--6--yl]carbamoyl}--L--threonine ( = N 6 --{{[(1S,2R)--l--Carboxy--2--hydroxypropyl]amino}carbonyl}adenosine, t 6 A) (V. Boudou, et al.). Stepwise Solid--Phase Synthesis of Peptide--Oligonucleotide Conjugates on New Solid Supports (M. Antopolsky & A. Azhayev). Influence of the Type of Junction in DNA--3'--Peptide Nucleic Acid (PNA) Chimeras on Their Binding Affinity to DNA and RNA (B. Greiner, et al.). Triple Helices of Optimally Capped Duplex DNA (sigma--DNA) with Homopyrimidine DNA and RNA at Neutral pH (W. Bannwarth & P. Iaiza). Synthesis of 5'--C-- and 2'--O--(Bromoalkyl)--Substituted Ribonucleoside Phosphoramidites for the Post--synthetic Functionalization of Oligonucleotides on Solid Support (X. Wu & S. Pitsch). Synthesis and Stability of GNRA--Loop Analogs (K. Worner, et al.). Synthesis of 3'--Thioamido--Modified 3'--Deoxythymidine 5'--Triphosphates by Regioselective Thionation and Their Use as Chain Terminators in DNA Sequencing (C. Wojczewski, et al.). Hydrolysis of Phosphodiester Bonds within RNA Hairpin Loops in Buffer Solutions: the Effect of Secondary Structure on the Inherent Reactivity of RNA Phosphodiester Bonds (I. Zagorowska, et al.). Duplex--Stabilization Properties of Oligodeoxynucleotides Containing N 2 --Substituted Guanine Derivatives (R. Eritja, et al.). Use of the Fluorescent Nucleoside Analogue Benzo[g--]quinazoline 2'--O--Methyl--beta--D--ribofuranoside to Monitor the Binding of HIV--1 Tat Protein or of Antisense Oligonucleotides to the TAR RNA Stem--Loop (A. Arzamanov, et al.). Solution Structure of a RNA Decamer Duplex, Containing 9--[2--O--(beta--D--ribofuranosyl)--beta--D--ribofuranosyl]adenine, a Special Residue in Lower Eukaryotic Initiator tRNAs (I. Layten, et al.). Solution Structure of a Hexitol Nucleic Acid Duplex with Four Consecutive T T Base Pairs (E. Lescrinier, et al.). Nonenzymatic Oligomerization Reactions on Templates Containing Inosinic Acid or Diaminopurine Nucleotide Residues (I. Kozlov & L. Orgel). Index.

Review :
"It will be a useful addition to the bookshelf of chemists working in the area of nucleosides and nucleic acids." (Perkin Transactions, No.13, 2001)