Synthetic Strategies and Parameters Involved in the Synthesis of Oligodeoxyribonucleotides According to the Phosphoramidite Method

Serge L. Beaucage1, Marvin H. Caruthers2

1 Center for Biologics Evaluation and Research, Food and Drug Administration, Bethesda, Maryland, 2 University of Colorado, Boulder, Colorado
Publication Name:  Current Protocols in Nucleic Acid Chemistry
Unit Number:  Unit 3.3
DOI:  10.1002/0471142700.nc0303s00
Online Posting Date:  May, 2001
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The phosphoramidite approach has had a major impact on the synthesis of oligonucleotides. This unit describes parameters that affect the performance of this method for preparing oligodeoxyribonucleotides, as well as a number of compatible strategies. Milestones that led to the discovery of the approach are chronologically reported. Alternate strategies are also described to underscore the versatility by which these synthons can be obtained. Mechanisms of deoxyribonucleoside phosphoramidite activation, factors affecting condensation, and deprotection strategies are discussed.

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Table of Contents

  • Accounts of Chemical Research in DNA Oligonucleotide Synthesis
  • Alternate Strategies to the Preparation of Deoxyribonucleoside Phosphoramidites
  • Activation of Deoxyribonucleoside Phosphoramidites
  • Factors Affecting the Condensation Rates of Deoxyribonucleoside Phosphoramidites
  • Significance of the “Capping” Reaction in the Chemical Synthesis of Oligodeoxyribonucleotides
  • The Oxidation Reaction in the Synthesis of Oligodeoxyribonucleotides According to the Phosphoramidite Method
  • Strategies in the Deprotection of Synthetic Oligodeoxyribonucleotides
  • Alternate Strategies to the Synthesis of Oligodeoxyribonucleotides According to the Phosphoramidite Method
  • Concluding Remarks
  • Literature Cited
  • Figures
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Literature Cited

Literature Cited
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