Overview of the Synthesis of Nucleoside Phosphates and Polyphosphates

David C. Johnson1, Theodore S. Widlanski1

1 Indiana University, Bloomington, Indiana
Publication Name:  Current Protocols in Nucleic Acid Chemistry
Unit Number:  Unit 13.1
DOI:  10.1002/0471142700.nc1301s15
Online Posting Date:  February, 2004
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This overview summarizes methodology used for the synthesis of nucleoside mono‐, di‐, and triphosphates. Selected techniques such as the Mitsunobu reaction, displacement reactions involving nucleoside 5′‐tosylates, “anion‐exchange” techniques, and phosphoramidite and phosphoramidate methodologies are highlighted. The chemistry of phosphorylation is detailed with respect to advantages and limitations under various conditions. Applicability of the methods toward the synthesis of analogs such as imidophosphates, phosphorothioates, and radiolabeled nucleotides is also addressed.

Keywords: nucleoside monophosphate; nucleoside diphosphate; nucleoside triphosphate; nucleotide synthesis; phosphorothioate; imidophosphate; nucleotide review

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Table of Contents

  • Issues Associated With Nucleoside Phosphorylaton
  • Chemical Reactivity of Nucleosides
  • Chemical Reactivity of Phosphorus
  • Reagents Used in Synthetic Nucleotide Synthesis
  • Nucleotide Analogs
  • 3′‐Phosphoadenosine‐5′‐Phosphosulfate (PAPS)
  • Cyclic Nucleoside Phosphates and Phosphorothioates
  • Enzymatic Nucleotide Synthesis
  • State of the Art
  • Literature Cited
  • Figures
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Literature Cited

Literature Cited
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