Chapter 1 : nucleobases with designed patterns of hydrogen bonding

Research output: Chapter in Book/Report/Conference proceedingChapter (peer-reviewed)

Abstract

The chemistry used in key bond-forming steps to prepare nucleobases with designed patterns of hydrogen bonding is surveyed. Incorporation of the nucleobases into DNA and RNA oligomers is achieved either chemically using building blocks such as nucleoside phosphoramidites or enzymatically using nucleotide triphosphates. By varying the hydrogen bonding pattern within nucleobases, and by incorporating additional substituents, new structures have been designed that "reach over" so that contacts with both strands in targeted duplex DNA can be made in antigene strategies to control gene expression. Various new base-pairing systems have been evaluated that expand the genetic alphabet beyond Watson-Crick base pairs A.T and G.C. For example, benzo-homologated analogs of the natural DNA bases represent a new genetic set of orthogonal, size-expanded derivatives that have been shown to encode amino acids of a protein in a living organism.
Original languageEnglish
Title of host publicationAdvances in heterocyclic chemistry
EditorsAlan R. Katritzky
PublisherElsevier
Pages1-39
Number of pages39
Volume107
ISBN (Print)978-0-12-396532-5
DOIs
Publication statusPublished - 2012

Publication series

NameAdvances in heterocyclic chemistry
PublisherAcademic press
ISSN (Electronic)0065-2725

Keywords

  • base pair
  • DNA
  • heterocycle
  • hydrogen bonding
  • nucleobase
  • pyridine-stretched
  • phosphoramidite

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  • Cite this

    Fraser, W. (2012). Chapter 1 : nucleobases with designed patterns of hydrogen bonding. In A. R. Katritzky (Ed.), Advances in heterocyclic chemistry (Vol. 107, pp. 1-39). (Advances in heterocyclic chemistry). Elsevier. https://doi.org/10.1016/B978-0-12-396532-5.00001-9